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 nearby Cape Ann Foodie Tours

Harbor Loop, Gloucester, Massachusetts 01930
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
    $486 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Gloucester are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 99 Rentals in Gloucester
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    0.7 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    0.9 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Good Harbor House  Vacation Rental-Walk to Beach1 / 12
    (15)Excellent
    1.8 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Waterfront 2 Bedroom !1 / 14
    (4)Excellent
    0.7 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
    Reviewed 25 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Remodeled 3BR Gloucester Annisquam River Cottage1 / 24
    (1)Excellent
    2.1 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1.8 kilometres from Cape Ann Foodie Tours
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. Walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor House”...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    2.8 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **There is a possibility that construction will ongoing near the property 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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
    Make Enquiry
    'Misselthwaite Manor' B&B1 / 23
    (4)Very good
    2.6 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2014
    Beautiful home. Open beam construction. Impressive wooden entry door with iron work fixtures. Soothing relaxing music playing in the breakfast room. Walled in yard with gated...
    Reviewed 6 September 2014
    We found the house to be in good order. The kitchen had everything we needed to cook once in a while when we didn't dine out. The bathrooms and bedrooms were nice and clean...
    See all reviews
    About this property
    'Misselthwaite Manor' is a a quiet respite in a busy world, yet close to everything Historic Gloucester has to offer. Bring your bikes, kayaks, SUP's and enjoy the beaches and wilds that Gloucester has to offer. Located in the heart of the private peninsula of Eastern Point, you can meander...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Dragonfly1 / 7
    (2)Excellent
    1.9 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed 30 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
    See all reviews
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Enquiry
    5.5 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North Shore, with 1.5 miles of pure...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Gloucester rentals sent straight to your email!
    Get the List
    3.5 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    2.0 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    4.3 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3.8 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Cable/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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    4.3 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, spacious open...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    0.6 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    1.9 kilometres from Cape Ann Foodie Tours
    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Cable/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
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    0.7 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in East Gloucester, Massachusetts wake up in a dramatic furnished waterfront 2 bedroom and one bathroom apartment living at the edge of Gloucester's Inner Harbor. The unit has hardwood floors with an open concept living with cathedral ceilings and windows galore ! Watch the sunset from a...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.8 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    2.0 kilometres from Cape Ann Foodie Tours
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed 25 October 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
    See all reviews
    About this property
    At the edge of Good Harbor Beach, 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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Captain John Stephens House: Sparkling new studio in the heart of Gloucester1 / 24
    (1)Average
    0.6 kilometres from Cape Ann Foodie Tours
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    When we walked into the rental, it was nicely decorated and very clean, but there were hidden problems. No air conditioning, and the damage deposit is nonrefundable. Had to...
    See all reviews
    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    1.8 kilometres from Cape Ann Foodie Tours
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and gracious vacation rental home offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family or your extended group of up to 16, making it the perfect getaway for family reunions or vacations with friends. The house has been...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    Make Enquiry
    1.9 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.0 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    0.9 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    2.1 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Cable/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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    1.9 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. This gracious home gives hints to a bygone era while offering modern amenities. A...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    3.5 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/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
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2.9 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the coast, the...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    2.0 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.9 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 entertainment...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    4.5 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    3.2 kilometres from Cape Ann Foodie Tours
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
    See all reviews
    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    2.0 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Cable/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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    4.2 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Patio
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficiently and effectively packs a...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    3.3 kilometres from Cape Ann Foodie Tours
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Close to Half Moon Bay1 / 12
    (1)Excellent
    1.9 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    3.6 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll enjoy swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. With a kayak, you can paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an acre...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Cher Ami: Gleaming and immaculate condo just 0.3 mi to Cressy's Beach1 / 17
    (1)Excellent
    1.8 kilometres from Cape Ann Foodie Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2016
    everything about this place was A+ ,the owners ,the apartment ,the location,the scenery,everything was awesome
    See all reviews
    About this property
    Welcome, cher ami ('dear friend'), to this gleaming and immaculate, second floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 bedrooms plus...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    0.8 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Porch
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting directly on the the beautiful port of Gloucester Harbor, this light and airy 3 room apartment offers full private bath, fully applianced kitchen, king bed and wonderful sitting porch. Walk or bike to local restaurants, museums, theatre and beach, and enjoy all that is Gloucester. The...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4.8 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway....
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3.0 kilometres from Cape Ann Foodie Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanside at Good Harbor is a waterfront vacation home directly on Good Harbor Beach, Gloucester's finest stretch of sand. Gracious and beloved, this family-friendly five bedroom summer cottage is set on picturesque Brier Neck. Sit on the waterfront terrace/patio and enjoy the summer breezes and...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    2.9 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Grill
    • Waterfront
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Beach views from almost every room --3 bedroom/3 bath home stylishly furnished with your beach vacation needs in mind. Just a 7 minute walk to Good Harbor Beach and lot's of space to play inside and out. Spacious rooms with hardwood floors, big kitchen to gather over meals, family room...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3.1 kilometres from Cape Ann Foodie Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern one bedroom apartment with a new kitchen and updated bathroom, inside our contemporary home above Good Harbor beach. Privately separated with the front door as the main entrance. Open concept kitchen+ living room with dining seating for 6! Cool place to rest after a long day at the...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    1.6 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.6 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2016! Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy the views of the sunrise. On a...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    0.9 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3.1 kilometres from Cape Ann Foodie Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean-view vacation rental home. Spend the day at the beach where you can swim, soak in the sun, or walk at low tide out to picturesque Salt Island. Prefer to stay at the house? Relax...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3.3 kilometres from Cape Ann Foodie Tours
    8 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your life. The home is situated between two of Cape Ann's most coveted beaches, Long Beach and Good Harbor Beach. The home is a stones throw away from an ice cream stand and pizza shop....
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 8 Bedrooms, 2 Bathrooms, Sleeps 16
    Make Enquiry
    0.7 kilometres from Cape Ann Foodie Tours
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Previous
    List your property
    Owner log in