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.

Cape Ann Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Price
    per night
    $441 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Cape Ann are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 146 Rentals in Cape Ann
    Sort by:
    Default
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Periwinkle Cottage - Unit 11 / 23
    (28)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    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...
    See all reviews
    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • DVD Player
    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed 3 August 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
    See all reviews
    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Wi-Fi
    • Patio
    • Ocean Views
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Salty Dog Summer Stay at Old Garden Beach1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed 19 February 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
    See all reviews
    About this property
    Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing spectacular views of...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Quaint Seaside Village Studio Steps  From Beach1 / 15
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
    Reviewed 20 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
    See all reviews
    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2016!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    AFFORDABLE GUEST ROOM BY BEACH, WALK EVERYWHERE!1 / 15
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • Private Garden
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
    Reviewed 17 October 2016
    Comfy and clean. You have you own private sitting area w/table, chairs, couch, library, TV. There's Keurig w/breakfast snacks and Wendy stocks the fridge w/drinks. You're...
    See all reviews
    About this property
    Are you looking for an affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and comfortable, for one or...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Oceanfront Cape Ann retreat w/ stunning  views, fireplace, deck, & gas grill!1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We made this rental last minute and were so glad that we were able to get it. It has a wow factor when you arrive. The back deck faces east, so you get the benefit of seeing a...
    See all reviews
    About this property
    Go on a classic New England retreat and enjoy a luxurious stay at this lovely Cape Ann home. You'll have amazing oceanfront views, a cozy wood-burning fireplace, and a great deck with a gas grill for outdoor entertaining. This house is located in Rockport, MA, just 43 miles northeast of the city of...
    View all property information
    Location Information
    Cape Ann, Massachusetts 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Cape Ann rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores and seafood markets. Dive...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    The Mariner - Authentic Rockport Experience1 / 24
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Parking
    • Waterfront
    • Air Conditioning
    • Terrace
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    We had a great experience at the Mariner. Even if we were a bit off-season, most of the shops & restaurants were open on Bearskin Neck. It's a picturesque town, what you...
    Reviewed 3 January 2017
    Justin is very helpful. The rental is right in the middle of the action in Rockport. The rental is completely modern with all amenities. The internet is even fast! This is a...
    See all reviews
    About this property
    The Mariner is a custom-furnished, luxury apartment with a panoramic harbor view and providing all the amenities and comfort that one may need to enjoy time in Rockport, Massachusetts. <BR><BR>The Mariner, a 2nd floor apartment, is located at 35 Bearskin Neck. The front entrance is on Bearskin...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Remodeled 3BR Gloucester Annisquam River Cottage1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
    See all reviews
    About this property
    Enjoy a peaceful retreat in coastal New England by staying at this lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will surely become a place...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Washer
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, MA, this home is a short walk...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Washer
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Labor Day Week- First week in September still AVAILABLE. from 9/2 to 9/9 - Book now ! Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full bathrooms, non obstructed...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual or couple...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
    • Satellite TV
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Parking was a little tricky and I have to say I was quite concerned when we first arrived. However, Tim was there to greet us and made sure we found appropriate parking for all...
    Reviewed 7 August 2017
    The Beach & King is the perfect vacation home for our four generation family. The house is spacious and beautifully decorated. The front porch is a lovely spot to enjoy...
    See all reviews
    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Enquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Good Harbor House  Vacation Rental-Walk to Beach1 / 12
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    My family and I have stayed at Good Harbor house for the past five or six years. We have been coming to Gloucester every year for more than 20 years. Good Harbor house is...
    See all reviews
    About this property
    This tastefully decorated, immaculate one-bedroom vacation rental is on the first floor of a landmark Victorian, with private entrance off a grand wrap-around covered veranda, overlooking private fenced-in lawn and garden. The covered veranda provides a great cooling respite from the sun in summer...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and recently renovated vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! Ideally situated just a short stroll from Old Garden Beach and the historic and quaint oceanfront village of Rockport, Beach Bound is a delightful and newly constructed 4 bedroom, 2.5 bath vacation home. Relax on the lovely back deck enjoying the home’s serene setting in a quiet,...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Front row seats from every room and deck to view glorious evening sunsets over the Annisquam River and Ipswich Bay. Sunset Cottage is a charming 2 bedroom, 1 bath cottage on Gloucester’s Thurston Point that sits directly on the tidal Annisquam River and boasts unparalleled views. Two decks with...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines is situated on over an acre of waterfront land and has lovely gathering spaces both inside and out. It was built as an impressive yet casual vacation home to entertain the family...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 5 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
    See all reviews
    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2016! Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout,...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful summer vacation rental cottage, overlooking broad stretches of the Atlantic Ocean and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of New England. The wraparound porch and expansive yard allow you to fully enjoy Cape Ann's natural beauty....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet and comfortable vacation rental cottage is just across the street from Folly Cove, one of the most striking coves on Cape Ann. The living room has views of the water (just across the street) and off of the living room is a nice screened porch with views and a granite floor. The large...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets you will experience from the deck or the delightful gazebo. This home has a brand new custom kitchen,...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Balcony
    • Satellite TV
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! This bright and open contemporary vacation rental home is the perfect home base for multiple families or groups, having two living rooms and two dining rooms and plenty of space to stretch out. There is also access to private Coffins Beach; choose to walk the .7 miles to the beach, or...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Patio
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boasting stunning views only imaginable from a home with direct water frontage, Spindrift, a 4+ bedroom, 2+ bath vacation rental home is located in Rockport’s lovely South End. It is the perfect location for rest and relaxation. According to the Oxford English Dictionary, a “Spindrift” is “spray...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
    Reviewed 2 July 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
    See all reviews
    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming vacation rental home is ideally situated just 300 yards from the waterfront, as well as a short walk (1 mile) to a sandy beach, and the picturesque village of Rockport with its shops, restaurants, galleries and the world class Shalin Liu Performance Center. Choose to cook your...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Golden Sands is the quintessential turn of the century Gloucester beach 'cottage.' With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house. The main level includes...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
    See all reviews
    About this property
    Formerly Seaward Inn, "The Seaward" continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Waterfront Woodsy 3BR Cottage1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
    See all reviews
    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is 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 courts, newly...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Waterfront
    • Internet Access
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor with unobstructed 180 degree views of the Atlantic, Sandy Bay, and the twinkling lights of the village of Rockport. The location of the home is ideal, away from all the hustle of town, but a 10 minute walk to...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Season-June through September- Aug 26 to Sept 9 (2 weeks in a row); Directly on the Atlantic with spectacular ocean views opposite Thatcher’s Island’s Twin Lights. Relax on the wooden deck off the 16 foot sliding glass doors from the living room/dining room. On the right of the house is a...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet and comfortable waterfront vacation rental cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. The main floor of the home consists of a charming open living and dining area, a small but well-equipped kitchen, a half bath, a screened...
    View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • DVD Player
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015 and brought up to the highest modern standard, it retains its old world charm. It has wonderful architectural...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Life is a voyage, and Way Point is the perfect place to launch part of your voyage. Way Point is not only the name of this adorable two bedroom vacation rental apartment, it also refers to a nautical sailing term which means 'a stop along the way, or a place to change course.' Enjoy air...
    View all property information
    Location Information
    Essex, Cape Ann 01929
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    The Pratt House on the Boulevard1 / 25
    (10)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    Nine of us gathered for a family Thanksgiving weekend in this lovely, roomy, comfortable home in Gloucester. Location was perfect - close to walking paths, beach and unique...
    Reviewed 18 November 2016
    Ambience,location, Comfort. this house is a true Home and has everything You could want or need. It was rented for a 10 year Reunion of a Marine squad. Four couples attended...
    See all reviews
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Ocean Views
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
    View all property information
    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Previous
    List your property
    Owner log in