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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
25–30 Aug
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4.93 out of 5 average rating, 185 reviews
Guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Nov
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 275 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Gloucester
Harbor View Apartment
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
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
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Guest suite in Rockport
Sandpiper's Suite
4.95 out of 5 average rating, 158 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
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
Home in Gloucester
Rocky Neck Retreat
4.99 out of 5 average rating, 221 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 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
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.93 out of 5 average rating, 15 reviews, 2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 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
Guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
4.99 out of 5 average rating, 162 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
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
Flat in Gloucester
Captain's Lookout | Roof Deck & Harbor Views
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept