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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, 308 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
2 bedrooms, 2 beds, 1 bathroom
4–9 Dec
4.93 out of 5 average rating, 124 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
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
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, 173 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
25–30 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
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 13 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
Home in Gloucester
Rocky Neck Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
19–25 Jul
4.99 out of 5 average rating, 221 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, 122 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, 243 reviews
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.99 out of 5 average rating, 138 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
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 275 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