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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
11–16 Jul
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
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
31 Aug – 5 Sept
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 168 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
5.0 out of 5 average rating, 22 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Guest favourite
Guest suite in Gloucester
Beachside~at Good Harbor Beach 2 person 1 bedroom.
4.95 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 135 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 216 reviews, 4 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
4.89 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 1 bathroom
27 Jul – 1 Aug
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
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
Top guest favourite
Home in Gloucester
Panoramic Ocean View; walk to private beach
4.97 out of 5 average rating, 90 reviews, 5 bedrooms, 8 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 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