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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 private bathroom
20–25 Sept
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4.99 out of 5 average rating, 134 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
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, 112 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
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 40 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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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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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, 51 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
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 31 reviews
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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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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, 92 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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Apartment in Gloucester
KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 202 reviews
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Flat in Gloucester
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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Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
10 bedrooms, 15 beds, 3 bathrooms
1–7 Sept
4.97 out of 5 average rating, 75 reviews
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Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 13 reviews
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Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 93 reviews
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Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds, 1.5 bathrooms
19–24 Sept
4.8 out of 5 average rating, 281 reviews