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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds, 1.5 private bathrooms
2–7 Nov
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4.99 out of 5 average rating, 82 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in Beverly
Cozy Boho Den
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 88 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 284 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Guest suite in Gloucester
The Artist Suite by Toi Moi
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Rockport
Waterfront Downtown Apartment • Walk Everywhere
1 bedroom, 3 beds, 1 bathroom
9–14 May
4.95 out of 5 average rating, 127 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 369 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.95 out of 5 average rating, 43 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 18 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, 132 reviews
Top guest favourite
Flat in Rockport
Downtown Rockport Stay with Private Ocean Deck
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Rockport
Rockport Studio w/parking|Walk 2 Downtown Rockport
1 queen bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 86 reviews