We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Ipswich, MA and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $380 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Ipswich is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    Applied filters:
    Nearby
    Clear All
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $285
    / Night
    Payment Protection
    View Details
    View Details
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $195
    / Night
    Payment Protection
    View Details
    View Details
    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $278
    / Night
    Payment Protection
    View Details
    View Details
    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $348
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Parking
    • Private Garden
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One of the few seaside old family cottages of Gloucester that is ready to welcome you for a unique experience. Fully equipped with a gorgeous view of colorful sunsets and a home that delivers a great living space near Halibut Point on the water. A very large home with 4 bedrooms and bunk room;... View all property information
    Location Information
    Ipswich, Massachusetts 01930
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $306
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Shared Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The most elegant room in the house with sitting area in front of a fireplace and private bath. Enjoy this charming New England B&B with scrumptious complimentary breakfast. Just a 5 minute walk to the sea river channel. 9.7% tax included. This home is one of the 59 First Period houses of Ipswich,... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $235
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Parking
    • Shared Garden
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A great experience in an old New England home renovated into a gracious bed & breakfast residence. Immediately be engrossed in the traditional feel of the old woodwork and flooring. An outside deck for warmer days and a fireplace sitting room for chilly evenings and winter days. The rooms include... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $220
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Wi-Fi
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Swedish Room is themed with open wood plank floors and hand-crafted bed cover. It is particularly cozy with sun-streamed angled dormers and built in closet and drawers. It can accommodate up to 4 people with its queen and twin beds. Private bath. One of New England's most charming B&Bs with... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    From
    $153
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Waterfront
    • Porch
    • Ocean Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    High-lights of Scandinavian design throughout the house will give a sense of tranquility as the breezes pass through a nice old-fashioned screen porch. Two large long tables for dining inside or out help to bring friends and family together. The kitchen, dining and porch space are the focus of this... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $209
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Terrace
    • Waterfront
    • Ocean Views
    • Outdoor Dining Area
    • Balcony
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled on Little Neck hill just a short walk to Pavilion beach and River Road beach across from Crane Beach, this home is cool and relaxing. Covered in giant old trees with distant views of Plum Island Sound and Ipswich River channel. Your get-away! This cottage is beautifully weather-worn and one... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    1 / 13
    5 of 5 stars (2) Excellent
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $557
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Shared Garden
    • Parking
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely, historic home B&B refurbished to offer guests modern amenities and a stylish comfortable stay. Conveniently located in the center of all to see. A few miles from 'Crane Beach', a five mile long bird sanctuary and top 10 ranked family beach. A short drive to Rockport, Gloucester, Essex,... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    5 of 5 stars Reviewed 8 June 2015
    Our stay at Rogers and Brown's B&B was fantastic. You feel like you have stepped back in time. Extremely comfortable beds and the attention to all the details one experts...
    5 of 5 stars Reviewed 23 April 2014
    Charming home with hosts who really care, and are very knowledgeable about the history. Very comfortable home and bed, breakfast of quiche and fresh fruit, better than average...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $235
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Shared Garden
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A charming New England B&B just a 5 minute walk to the sea river channel. Complimentary breakfast and wifi included. This room is spacious with a mini-kitchen including a microwave and Keurig coffee maker. Private bath. Price includes 9.7% tax. The home is charmingly antique and yet updated for... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $125
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Outdoor Dining Area
    • DVD Player
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Space If you've read this far, you must be interested in renting this gem for the whole 4 months, May 15 to September 15. No exceptions, as of now. A traditional small Great Neck clam shack cottage right in front of the water with a stunning view of Plum Island Sound. Set up as a 1 bedroom... View all property information
    Location Information
    Ipswich, Massachusetts 01938

    The following rentals are within 15 kilometres of Ipswich, Massachusetts.

    1 / 28
    5 of 5 stars (4) Excellent
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    From
    $452
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that provides refreshment from the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 6 October 2015
    From first contact with Marilyn, she was responsive, informative and a pleasure to talk to. I explained what me and my friends were looking for (a weekend get-away) and she was...
    5 of 5 stars Reviewed 18 August 2015
    We had a great time at the Pratt House and recommend both the home and the area. There's plenty to do in the area and lots of space to spread out within the home. We were very...
    See all reviews
    1 / 26
    5 of 5 stars (11) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    $1,949
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 7 July 2015
    I have stayed in a dozen or so vacation rentals over the years, including several in the Cape Anne area, and this one was by far the best maintained, best outfitted, most...
    5 of 5 stars Reviewed 6 October 2013
    My wife and I stayed a week at Summerwind in September. The house overlooks Gloucester harbor, and although close to the center of town and near restaurants and shops, it is...
    See all reviews
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $209
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    other travellers have booked this property
    From
    $696
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, dryer. Three fireplaces,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 26
    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $3,480
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this condo sleeps 8+ in centrally air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named beach is one mile long spanning both the community of Gloucester and Rockport - take your... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    From
    $4,177
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One acre up on quiet bluff, with new view deck and windows overlooking the best beach north of Boston, is our four bedroom, two bath house with lots of parking and just 1500 yards from the ocean. Come and stay with your family or friends and enjoy Good Harbor Beach and all of historic and original... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 50
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    From
    $3,132
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Porch
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. From the side entrance on a quiet lane, you will step into a bright back hall with... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 29
    Beverly
    4 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
    From
    $4,873
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Hastings Retreat, a 4 bed/3.5 bath vacation rental home, is located in desirable Beverly Cove and includes rights to Brackenbury beach, a large sandy beach which is shared by a just a handful of neighbors. The house is privately situated just 3 properties away from the beach as well as 2.5 miles... View all property information
    Location Information
    Beverly, Massachusetts 01915
    Get the List
    1 / 25
    Prides Crossing
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $459
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in desirable Beverly Farms this delightful larger unit of the estate's carriage house, includes shared use of the swimming pool, tennis court, private beach and hot tub. Just half a mile away is West Beach, which is open only to residents of Beverly Farms. Enjoy the amazing outdoor... View all property information
    Location Information
    Prides Crossing, Massachusetts 01915
    1 / 26
    5 of 5 stars (2) Excellent
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    From
    $160
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Wi-Fi
    • Patio
    • DVD Player
    • Outdoor Dining Area
    • Central Heating
    • Washer
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This eclectic STUDIO PLUS is decorated in a charming, boho style with creative objects d'art and romantic/atmospheric lighting (which makes for a wonderfully cozy retreat) A petite solarium brings morning light, along with one large skylight in bathroom. The beautifully designed outdoor covered... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
    5 of 5 stars Reviewed 25 January 2015
    We stayed here and had a delightful week in Gloucester ~ a cozy, romantic and uniquely decorated apartment ~ very aesthetic with extra ammenties ( ie, a washer & dryer) and a...
    See all reviews
    Gloucester
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    From
    $3,480
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Private Garden
    • Satellite TV
    • Secure Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    At the edge of one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage with great on-beach... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 25
    Essex
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    From
    $2,718
    / Week
    View Details
    View Details
    Amenities & Details
    • Patio
    • Porch
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful vacation rental home offers gracious comfort and easy access to the riverfront town of Essex, with its multitude of antique shops and restaurants, including the inventor of the fried clam - Woodman's. Enter the home via the stately front porch complete with rocking chairs, making... View all property information
    Location Information
    Essex, Cape Ann 01929
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $6,682
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Grill
    • Ocean Views
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house just steps from the private end of Good Harbor Beach. Open and airy living space with spectacular views of the beach, modern kitchen with all the amenities, large dining area for... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Plum Island
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    From
    $496
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Available 10/1 through October. Winter Rental potential after summer; please contact. New construction home (08) offers 3 bedrooms and 3 baths sleeps 10/12.. Large master with full walk in closet and master bath. Beautiful hardwood floors, open concept, and ocean and marsh views make for a... View all property information
    Location Information
    Plum Island, Massachusetts 01951
    Newbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $1,740
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Porch
    • DVD Player
    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming, newly renovated cottage on Plum Island basin, new front and back decks, all new appliances, refinished hard wood floors, beautiful views. Walking distance to main beach, private beach on basin, perfect for children, swimming, and kayaking. Newburyport is a 10 minute car ride and hosts a... View all property information
    Location Information
    Newbury, Massachusetts 01951
    1 / 28
    Prides Crossing
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $383
    / Night
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    On a gorgeous estate, this Beverly Farms Carriage house has been lovingly renovated and made into 3 tasteful and comfortable units. This air conditioned rental includes use of the estate swimming pool, tennis court, private beach, and hot tub. It is located just a half a mile from West Beach which... View all property information
    Location Information
    Prides Crossing, Massachusetts 01915
    1 / 43
    4 of 5 stars (1) Very good
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    From
    $3,272
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely cottage set high up on a hill overlooking the private section of Wingaersheek Beach, this lovingly restored 3 bedroom home has been in the same family for over 55 years. The cottage boasts one of the most spectacular hilltop views on the entire beach with meticulously maintained lawn and... View all property information
    Location Information
    Gloucester, Cape Ann 02116
    4 of 5 stars Reviewed 20 July 2015
    Great beach get away. Walk to private beach. Cottage was very cute and clean with nice deck, outdoor shower, and pretty gardens. Cottage was well equipped with linens, towels...
    See all reviews
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $696
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    From
    $2,924
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Shared Garden
    • Washer
    • Parking
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cozy two bedroom late 1800's home with updated big kitchen and two bathrooms. TV room, sitting room downstairs. Two bedrooms, full bath and walk in closet upstairs. Shared yard with BBQ grill, outdoor shower. Conv. store and gas station across the street. East Main is a busy street during the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 30
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $940
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • DVD Player
    • Porch
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy the best sunsets on the East Coast from this amazing riverfront classic Victorian summer retreat. Annisquam Singing Pines offers everything you could want in a vacation rental home. The house is situated on over an acre of waterfront land and has lovely gathering spaces both inside and out.... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $1,323
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This newly renovated, fully furnished,1 bedroom apartment is in a lovely, turn of the century home on Rocky Neck. It includes a full size sleep sofa in the living room, an eat-in kitchen, a large private deck with a gorgeous view of Smiths Cove, and a small office area with desk, phone and hi speed... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 25
    Beverly
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $2,297
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Grill
    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Toast the glow of another gorgeous day on the riverfront wraparound deck of Afternoon Delight in historic Beverly. A decorative columned portico and farmer's porch welcome you into to this immaculate and restful vacation rental home. Start in the foyer which opens to a carpeted living room with... View all property information
    Location Information
    Beverly, Massachusetts 01915
    1 / 4
    5 of 5 stars (1) Excellent
    Beverly
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $209
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Starting to book the season. A great place for graduations, weddings, Grand parents too.. Perfect for two- a place to put up family or friends for vacation or holiday time.This one bed room duplex in an attached renovated barn is just a short walk to Salem, 5 minutes from public transport to... View all property information
    Location Information
    Beverly, Massachusetts 01915
    5 of 5 stars Reviewed 10 July 2015
    We had an extremely stressful week in Boston with some last minute AirBNB cancellations, and when we weren't even able to find a hotel in Boston we lucked into finding this...
    See all reviews
    1 / 20
    4 of 5 stars (2) Very good
    Essex
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    From
    $348
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Balcony
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly remodeled luxury air conditioned townhome with views of the Great Marsh and Essex river from every room. New master bathroom with separate freestanding soaking bathtub and large shower, heated floors, and granite counter top. The master bedroom has a king size bed, ceiling fan, individual air... View all property information
    Location Information
    Essex, Cape Ann 01929
    3 of 5 stars Reviewed 13 October 2015
    Not as secluded as photos make it look. Owner lives on premises. Just in case you're expecting to be alone. We thought it should have been mentioned in the details. Gorgeous...
    5 of 5 stars Reviewed 17 June 2015
    I booked this accommodation for my in-laws who had never been on the North Shore before. The location can't be beat. Every morning we had breakfast (sometimes brunch!) overlooking...
    See all reviews
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $194
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Central Heating
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A small apartment above historical building and just a 7 minute walk (.4 mi) to Plum Cove Beach. Newly renovated and furnished. Utilities included (heat, wifi, water, elect). Hipster neighborhood with a cool cafe and boutiques. Laundry in bldg. Room type: Entire home/apt Bed type: Real Bed... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 28
    Newburyport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $139
    / Night
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SEPTEMBER 2015 UPDATE: We have rented this property with a long term tenant at the moment. - Thank you for your interest. Perfect for a professional on assignment, a visiting couple who want to to be a walkable distance from downtown Newburyport, anyone in housing transition. Description... View all property information
    Location Information
    Newburyport, Massachusetts 01950
    South Hamilton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $590
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • DVD Player
    • Washer
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Offering breathtaking ocean and marina views, this spacious apartment is sure to provide the perfect holiday experience. A large lounge room with modern comfortable furnishings including large screen Plasma Television and Austar allows for relaxation after a busy day on the island. The modern... View all property information
    Location Information
    South Hamilton, Massachusetts 4803
    Beverly
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    From
    $348
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Parking
    • Waterfront
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to the Harborfront House, located at historic Independence Park and Beach on Lothrop Street, recently recognized by the Boston Globe as one of the “20 Best Streets in Boston and Beyond'. You will be instantly captivated by the waterfront activity just steps from the front... View all property information
    Location Information
    Beverly, Massachusetts 01915
    1 / 6
    4 of 5 stars (1) Very good
    Gloucester
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $458
    / Night
    View Details
    View Details
    Amenities & Details
    • Waterfront
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located on the Northeast shore of Cape Ann, affording sweeping views of Ipswich Bay, with gorgeous summer sunsets over the water. It is nestled in among three other waterfornt cottages in a quiet... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed 27 September 2015
    We stayed at this glouster harbor house for a wedding weekend. Ten of us stayed comfortably. The house is furnished with everything you need. Dr. Rick was wonderful with prior...
    See all reviews
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other traveller has booked this property
    From
    $103
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Terrace
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Balcony
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Not just near the harbor. ON the harbor. A perfect scene all year-round across the bay of the Harbor, Ten Pound Island and the Paint Factory. Walk easily to harbor restaurants, supermarket, train, THE BEACH. A casual home with exceptional views. The Space This is a privileged spot on Gloucester... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 11
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $388
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Balcony
    • Internet Access
    • Terrace
    • Grill
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The cottage is an updating of the original Coggeshall artist camp overlooking a grassy acre of land leading to its own point of land jutting into Ipswich Bay. With prevailing calm water the shorefront is usable for swimming and boating (boat launch 1/2 mile at Lane's Cove). The cottage is at the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    other travellers have booked this property
    From
    $597
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    **There is a possibility that construction will ongoing next door during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as well as two... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 17
    Gloucester
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    From
    $519
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Captain John Stephens House is a newly remodeled studio condo unit located in downtown Gloucester. This bright and modern studio makes a perfect summer vacation home for an individual or couple and a cozy retreat in the off-season. This beautiful furnished studio has an eat in granite kitchen and... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 35
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    From
    $348
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy this comfortable recently renovated 3 bedroom, 1 bath vacation home conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 30
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $2,297
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Porch
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Taking its name from the glorious sunsets one has the privilege of viewing from each of its rooms and both of its decks, Sunset Cottage is a renovated 2 bedroom, 1 bath cottage in Gloucester’s Thurston Point district. Sunset Cottage sits directly on the tidal Annisquam River and boasts air... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 30
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    $4,177
    / Week
    View Details
    View Details
    Amenities & Details
    • Porch
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 29
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $5,569
    / Week
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful and charming vacation rental home is ideally situated just one block from Good Harbor Beach overlooking the sand and the surf. Four bedrooms and two full baths, the house is well laid out and has fantastic views of the beach. Enter into the center stair foyer and on your left is a... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 8
    4.5 of 5 stars (4) Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    From
    $1,267
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on East Main street, so busy during the day, quiet at night. Close to everything by foot or bicycle. $1,150 off season monthly rate from Nov to April. 30 day minimum off season. New gas... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 9 September 2015
    This place is so well-located, well-designed, comfortable and easy! It allowed us a much needed break with access to all the beauty of Gloucester. I loved rocky neck, biking to...
    5 of 5 stars Reviewed 5 August 2015
    This is the perfect cottage for a couple retreat. It is a home away from home. Conveniently located for walks and picture taking. We will defintely stay here again when we...
    See all reviews