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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
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4.96 out of 5 average rating, 306 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
New place to stay, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.91 out of 5 average rating, 11 reviews, 2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Guest favourite
Flat in Gloucester
Artist Retreat
4.92 out of 5 average rating, 24 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 171 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Flat in Gloucester
Walk to Good Harbor Beach
4.93 out of 5 average rating, 131 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 121 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
4.99 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
22–29 Aug
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
4.92 out of 5 average rating, 240 reviews, 1 bed, 1 bathroom
17–22 Oct
Guest favourite
Flat in Gloucester
Fish & Ships on River: Steps to Ocean, Blvd, Park
4.91 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
4.99 out of 5 average rating, 158 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
4.96 out of 5 average rating, 150 reviews, 1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct