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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds, 3 private bathrooms
31 Aug – 5 Sept
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4.98 out of 5 average rating, 46 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
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
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
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
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
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
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
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 120 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 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
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
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
4.96 out of 5 average rating, 219 reviews, 1 bedroom, 3 beds, 1 bathroom
4–9 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
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
Apartment in Rockport
Waterfront Downtown Apartment • Walk Everywhere
4.95 out of 5 average rating, 117 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 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
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 suite in Rockport
Historic Rockport Large Suite, Entire Third Floor.
4.99 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept