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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
4–9 Apr
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4.92 out of 5 average rating, 254 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
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Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.97 out of 5 average rating, 146 reviews
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Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Nov
4.98 out of 5 average rating, 98 reviews
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Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds, 2.5 bathrooms
3–8 Nov
4.98 out of 5 average rating, 111 reviews
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Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 30 reviews
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Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
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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, 59 reviews
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Superhost
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 28 reviews
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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
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Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 34 reviews
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Superhost
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 101 reviews
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Home in Annisquam
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
New place to stay
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Home in Annisquam
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 39 reviews
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Flat in Gloucester
Charming 2BR•Walk to Harbor & Downtown•Close2Salem
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 35 reviews
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Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 62 reviews
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Flat in Rockport
Folly Cove Waterside
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 8 reviews
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Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 50 reviews
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Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
4.96 out of 5 average rating, 46 reviews