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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
,
4.96 out of 5 average rating, 306 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
New place to stay
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.93 out of 5 average rating, 43 reviews
Guest favourite
Flat in Gloucester
Artist Retreat
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
4.92 out of 5 average rating, 24 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Gloucester
Walk to Good Harbor Beach
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.93 out of 5 average rating, 131 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 121 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
1 bedroom, 2 queen beds, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed, 1 bathroom
17–22 Oct
4.92 out of 5 average rating, 240 reviews
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
3 bedrooms, 3 queen beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 88 reviews
Top guest favourite
Apartment in Rockport
Waterfront Downtown Apartment • Walk Everywhere
1 bedroom, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 117 reviews
Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds, 1.5 bathrooms
22–29 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 158 reviews
Guest favourite
Flat in Gloucester
Fish & Ships on River: Steps to Ocean, Blvd, Park
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 220 reviews