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Holiday Villas in Gloucester, MA

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All 26 Rentals in Gloucester
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From
£276
Per Night
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1 / 18
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House Rental - 
5 Bedrooms, 2 Bathrooms, Sleeps 13
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£70
Per Night
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1 / 22
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House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 8
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From
£209
Per Night
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1 / 28
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House Rental - 
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
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From
£96
Per Night
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1 / 5
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Apartment - 
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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, queen 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
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From
£64
Per Night
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1 / 7
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House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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
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From
£211
Per Night
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1 / 43
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Cottage - 
3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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
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From
£450
Per Night
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1 / 16
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House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A Great big space for family fun at the beach, in the kitchen and hanging out in the garden. This is not your ordinary summer cottage...everything is new, comfortable and set-up for year-round living. Just a 5 minute walk to the sand, and a great place to start a morning run on the backshore of... View all property information
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From
£209
Per Night
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1 / 9
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House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Awesome East Gloucester house with picture perfect view! Sip cocktails and watch the boats go by. Walk to Rocky Neck for great dining, art galleries, and more. Enjoy the music from the Neck while sitting on your own deck. A short walk to Niles Beach, bring your bikes or running shoes and run or... View all property information
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From
£64
Per Night
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1 / 8
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Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • 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. Sunny, furnished, adorable 1BD Living Room/Kitchenette downstairs, Bedroom/Bath upstairs. Discounted for longer stays. Nestled among yacht yards, Gloucester Stage Co., Pirate's Lane, and Rocky Neck... View all property information
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4 of 5 stars Reviewed 15 August 2014
Recommend it to couples only, quaint, very clean cottage in a busy area. Take caution pulling out of driveway. Bathroom upstairs a little small not much head room for those over...
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From
£8
Per Night
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1 / 4
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Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Title Travelers see this first while they are browsing properties, so be sure your title stands out. Description Give travelers an idea of what to expect from a stay in your rental. What is the space like? What's nearby? What makes it special? Give travelers an idea of what to expect from a stay... View all property information
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From
£418
Per Night
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1 / 18
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House Rental - 
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
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From
£129
Per Night
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1 / 16
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House Rental - 
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (15) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Good Harbor House consists of a one bed vacation renal and a spacious private entrance guest suite. We are located just one block up from Good Harbor Beach and scenic 'Back Shore' ocean walk-way. One mile to Gloucester Harbor and Rocky Next Art Colony. Three Miles to Rockport Center. We call your... View all property information
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5 of 5 stars Reviewed 3 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, hands...
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From
£147
Per Night
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1 / 27
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • 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
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5 of 5 stars Reviewed 2 September 2013
Have just spent a week at the cottage and it was was absolutely lovely. It is exactly like the pictures, beautifully decorated and very well equipped. The owners, Linda and Hank...
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From
£298
Per Night
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1 / 29
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This oceanfront year round home was recently constructed to maximize spectacular ocean views and sunsets. Enjoy the views of the water outside while sitting on the glassed in balcony just off of the master bedrooms , the screen/glass windows across the front or on the stone patio or dock. Inside,... View all property information
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5 of 5 stars Reviewed 3 October 2012
We were two families (four adults, 3 children and a toddler), and everyone had a wonderful time. Wingarsheek and Crane Beaches are reasonably convenient, as are some great...
5 of 5 stars Reviewed 1 May 2012
We were eight women celebrating over 50 years of friendship with a long weekend getaway. We were delighted with The Landry Cottage. The spacious house is brightly and...
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From
£96
Per Night
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1 / 17
Apartment - 
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
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From
£161
Per Night
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1 / 7
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
In historic Gloucester, MA. 2 blocks from Plum Cove Beach in one direction, Lanes Cove ( for boating and kayaking) in the other. Three miles from Rockport, 2 miles from Halibut Point, beautiful coastal state park. Quiet neighborhood, wonderful views View all property information
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2 of 5 stars Reviewed 7 August 2014
It's more like peek a boo views, in a nice neighborhood. There is so much junk in the cupboards there's no place to put your food or other things you might bring. The rest of the...
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From
£151
Per Night
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1 / 30
House Rental - 
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Enjoy the views, breezes and smell of the sea from this lofty perch overlooking Gloucester's famed waterfront Stacey Boulevard which is centered by the iconic 'Gloucester Fisherman at the Wheel' sculpture - a symbol of the fishing port's rich history, both as a working waterfront and as the subject... View all property information
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From
£1,102
Per Night
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1 / 51
House Rental - 
5 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
LUXURY OCEANFRONT ESTATE CLOSE TO BOSTON This truly unique, breathtaking oceanfront circa 1890 estate has been painstakingly renovated and modernized by its current owner. The property consist of close to 4 acres of direct oceanfront access with a 4,000 sf stone house that boasts an attached... View all property information
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From
£253
Per Night
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1 / 10
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Hot Tub
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Walk to Gloucester's best beach - Good Harbor just 2/10 mile from this wonderful duplex offering 3 air conditioned bedrooms and two full custom tile baths with showers. Enter into the open concept living, dining and kitchen areas with parquet floors which is the perfect place for your family to... View all property information
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From
£183
Per Night
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1 / 52
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
NEW IN 2013: Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 – December 31.This newly renovated and updated waterfront gem has four bedrooms and 1.5 baths, a deep-water dock (accommodates up to a 20 foot boat) and a wrap-around screened porch... View all property information
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From
£202
Per Night
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1 / 6
Cottage - 
4 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
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From
£298
Per Night
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1 / 14
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in the Private Section of Wingaersheek Beach (Coffin's Beach)and just a 3 minute walk to to the beach. Enjoy this totally renovated 4 bedroom ranch house with all the comforts of home! Central air, washer/dryer, fully equipped kitchen with sliders leading to a deck with a gas grill. New... View all property information
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From
£179
Per Night
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1 / 4
Cottage - 
5 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
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From
£271
Per Night
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1 / 8
House Rental - 
5 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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 house 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 full bath and... View all property information
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From
£229
Per Night
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1 / 8
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
7 Minutes walk to Downtown or train to Boston. Ideal quiet location & just minutes walk to 2 beaches. Weekly & Monthly Rentals Only Must Be Booked Months In Advance Of Arrival Date. I never do Daily rentals 4 Bedrooms, 3 with King sized beds. 2 Full Tub/Shower bathrooms. Off... View all property information
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From
£202
Per Night
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1 / 16
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Ours is a wonderful home. It's on a hill and 3-acres of woods and lawns overlooking Lobster Cover. Gloucester and Rockport are nearby and lovely places to stroll, dine and enjoy music. Boston's an easy train ride away and the highway's nearby as well. The 100-year old house is light and... View all property information
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