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Search results; Over 1,000 homes in Gloucester

Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 private bathroom
1–6 Nov
,
4.86 out of 5 average rating, 138 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 276 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Superhost
Flat in Gloucester
Chic Gloucester Escape~Walk 2 ShopsHarbor&Dining
4.89 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Gloucester
Ocean View | Walk to Downtown & Beach | Skylight
4.98 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
4.99 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 139 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Room in Gloucester
Spacious Private Suite w/ Bath in Lanesville
New place to stay, 1 queen bed, 1 bathroom
2–7 Aug
Top guest favourite
Room in Gloucester
Suite Magnolia
5.0 out of 5 average rating, 60 reviews, 1 king bed, 1 bathroom
2–7 Aug
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
4.92 out of 5 average rating, 244 reviews, 1 bed, 1 bathroom
4–9 Apr
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
4.88 out of 5 average rating, 142 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Aug
Top guest favourite
Guest house in Rockport
Seagull’s Nest
5.0 out of 5 average rating, 53 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Guest suite in Gloucester
The Artist Suite by Toi Moi
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Aug
Guest favourite
Home in Gloucester
1 Mi to Beach! Family Gloucester Gem w/ Yard
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 4 beds, 2 bathrooms
11–16 Apr
Top guest favourite
Cottage in Rockport
Cozy Oceanfront Beach Cottage - Walk to Downtown
4.96 out of 5 average rating, 27 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
4.93 out of 5 average rating, 71 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
Artist Retreat
4.92 out of 5 average rating, 25 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Top guest favourite
Guest suite in Rockport
Historic Rockport Large Suite, Entire Third Floor.
4.99 out of 5 average rating, 156 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept