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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
2 bedrooms, 3 beds, 1 private bathroom
7–12 Feb
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4.97 out of 5 average rating, 152 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
New place to stay, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 6 beds, 1 bathroom
23–28 Aug
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
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 170 reviews, 3 bedrooms, 3 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
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
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
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
4.98 out of 5 average rating, 51 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Gloucester
Cozy Apartment at Green Landing, No Cleaning Fee
4.97 out of 5 average rating, 66 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
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
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 120 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
4.97 out of 5 average rating, 88 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 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
Superhost
Flat in Rockport
Garden Getaway
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
4.96 out of 5 average rating, 220 reviews, 1 bedroom, 3 beds, 1 bathroom
4–9 Sept
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
5.0 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 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