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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
28 Aug – 2 Sept
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4.93 out of 5 average rating, 183 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
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
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
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 169 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
Flat in Gloucester
Sunsets on the Seawall
New place to stay, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
4.95 out of 5 average rating, 40 reviews, 3 bedrooms, 6 beds, 3 bathrooms
9–14 Jul
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
4.91 out of 5 average rating, 76 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, 119 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Guest favourite
Home in Gloucester
Brand new home minutes to the ocean
4.94 out of 5 average rating, 63 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Gloucester
Pavilion Beach Townhouse
4.97 out of 5 average rating, 67 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
4.99 out of 5 average rating, 82 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul