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Holiday Rentals and Homes in Gloucester, MA

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    From
    €445
    / Night
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    5 Bedrooms, 3 Bathrooms, Sleeps 11
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    From
    €289
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    1 / 28
    5 of 5 stars (3) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12
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    €133
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    1 / 22
    4 of 5 stars (4) Very good
    4 Bedrooms, 7 Bathrooms, Sleeps 8
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    €133
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    • Shared Tennis Court
    • Dryer
    • Refrigerator
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Gloucester, Cape Ann 01930
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    €111
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    1 / 9
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
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    Amenities & Details
    • Grill
    • Water Views
    • Air Conditioning
    • Waterfront
    • TV
    • Refrigerator
    • Wi-Fi
    • Cooker
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on East Main street, so busy during the day, but close to everything by foot or bicycle. $1,250 off season monthly rate from Nov to April. Sunny, furnished, adorable 1BD. Living... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 5 August 2015
    This is the perfect cottage for a couple retreat. It is a home away from home. Conveniently located for walks and picture taking. We will defintely stay here again when we...
    4 of 5 stars Reviewed 15 July 2015
    We stayed here with our 2 teenage boys who "bunked" in living room, the space was just enough an having all amenities (sat tv, wi fi, bbq...) was a bonus. The walks to the...
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    €382
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    5 Bedrooms, 2 Bathrooms, Sleeps 13
    other travellers have booked this property
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    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Washer
    • Satellite TV
    • Stereo System
    • Internet Access
    • Dryer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    **There is a possibility that construction will ongoing next door during the summer of 2015** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as well as two... View all property information
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    Gloucester, Cape Ann 01930
    From
    €2,669
    / Week
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    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dryer
    • Stereo System
    • Deck
    • Washer
    • Internet Access
    • DVD Player
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One acre up on quiet bluff, with new view deck and windows overlooking the best beach north of Boston, is our four bedroom, two bath house with lots of parking and just 1500 yards from the ocean. Come and stay with your family or friends and enjoy Good Harbor Beach and all of historic and original... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €594
    / Week
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    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Overview
    Amenities & Details
    • TV
    • Wi-Fi
    • Ocean Views
    • Water Views
    • Balcony
    • Secure Parking
    • Waterfront
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Not just near the harbor. ON the harbor. A perfect scene all year-round across the bay of the Harbor, Ten Pound Island and the Paint Factory. Walk easily to harbor restaurants, supermarket, train, THE BEACH. A casual home with exceptional views. Large kitchen and dining area with a view of the... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €2,002
    / Week
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Internet Access
    • Water Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Boat Available
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €289
    / Night
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Parking
    • Dryer
    • Ceiling Fans
    • Washer
    • Deck
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Gloucester, Cape Ann 01930
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    From
    €2,091
    / Week
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    1 / 43
    4 of 5 stars (1) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Watersports Nearby
    • Stereo System
    • Water Views
    • Waterfront
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely cottage set high up on a hill overlooking the private section of Wingaersheek Beach, this lovingly restored 3 bedroom home has been in the same family for over 55 years. The cottage boasts one of the most spectacular hilltop views on the entire beach with meticulously maintained lawn and... View all property information
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    Location Information
    Gloucester, Cape Ann 02116
    4 of 5 stars Reviewed 20 July 2015
    Great beach get away. Walk to private beach. Cottage was very cute and clean with nice deck, outdoor shower, and pretty gardens. Cottage was well equipped with linens, towels...
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    From
    €3,736
    / Week
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    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • TV
    • Deck
    • Ocean Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house just steps from the private end of Good Harbor Beach. Open and airy living space with spectacular views of the beach, modern kitchen with all the amenities, large dining area for... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €111
    / Night
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    1 / 25
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
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    Overview Reviews (2)
    Amenities & Details
    • Washer
    • Wi-Fi
    • Deck
    • DVD Player
    • Dryer
    • Central Heating
    • Stereo System
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This eclectic STUDIO PLUS is decorated in a charming, boho style with creative objects d'art and romantic/atmospheric lighting (which makes for a wonderfully cozy retreat) A petite solarium brings morning light, along with one large skylight in bathroom. The beautifully designed outdoor covered... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
    5 of 5 stars Reviewed 25 January 2015
    We stayed here and had a delightful week in Gloucester ~ a cozy, romantic and uniquely decorated apartment ~ very aesthetic with extra ammenties ( ie, a washer & dryer) and a...
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    From
    €1,245
    / Week
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    1 / 26
    5 of 5 stars (11) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    Overview Reviews (11)
    Amenities & Details
    • Deck
    • Washer
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 8 July 2015
    I have stayed in a dozen or so vacation rentals over the years, including several in the Cape Anne area, and this one was by far the best maintained, best outfitted, most...
    5 of 5 stars Reviewed 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
    €2,224
    / Week
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    1 / 29
    5 of 5 stars (10) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 12
    Overview Reviews (10) Make Enquiry
    Overview Reviews (10)
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Deck
    • Internet Access
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Gloucester, Cape Ann 01930
    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
    €279
    / Night
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    1 / 6
    4 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Waterfront
    • Internet Access
    • DVD Player
    • Satellite TV
    • Water Views
    • Washer
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located on the Northeast shore of Cape Ann, affording sweeping views of Ipswich Bay, with gorgeous summer sunsets over the water. It is nestled in among three other waterfornt cottages in a quiet... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €248
    / Night
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    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Deck
    • Internet Access
    • Washer
    • Satellite TV
    • Dryer
    • Stereo System
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The cottage is an updating of the original Coggeshall artist camp overlooking a grassy acre of land leading to its own point of land jutting into Ipswich Bay. With prevailing calm water the shorefront is usable for swimming and boating (boat launch 1/2 mile at Lane's Cove). The cottage is at the... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €391
    / Night
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    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Porch
    • Water Views
    • Fireplace
    • Refrigerator
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This lovely three bedroom/ two bath Victorian brings you back to an era when life was more serene and relaxed. In this idyllic and private area with woods on two sides, one can sit on the wraparound farmer's porch or on the screened porch, overlooking a glimmering lily pond, and almost forget it... View all property information
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    Location Information
    Gloucester, Cape Ann 01930
    From
    €1,525
    / Night
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    1 / 51
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • DVD Player
    • Washer
    • Satellite TV
    • Stereo System
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Gloucester, Cape Ann 01930
    From
    €254
    / Night
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    1 / 52
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Satellite TV
    • Deck
    • Stereo System
    • Water Views
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 3 February 2015
    We try to stay here every year because we love the comfortable quality of a vacation home that's been in the family since 1929. The roomy screened in porch wraps around 3 sides...
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    From
    €3,203
    / Week
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    1 / 45
    4 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Deck
    • Water Views
    • Patio
    • DVD Player
    • Grill
    • Satellite TV
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This stately home perched on the dramatic coast of East Gloucester, known locally as “Bass Rocks”, can accommodate ten-plus comfortably, making it the perfect gathering place for friends and family to enjoy the sounds, scents, and views of the Atlantic Ocean. The waterfront property boasts a... View all property information
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    Location Information
    Gloucester, Cape Ann 01930