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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Apartment in Gloucester
KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
2 bedrooms, 2 beds, 1 private bathroom
9–14 Nov
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4.96 out of 5 average rating, 205 reviews
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Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.97 out of 5 average rating, 149 reviews
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Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds
3–8 Nov
4.98 out of 5 average rating, 114 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 28 reviews
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Villa in Manchester-by-the-Sea
Secluded 20 Acre 10BR ultra contemporary Retreat
10 bedrooms, 15 beds
29 Sept – 5 Oct
4.97 out of 5 average rating, 75 reviews
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Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
3–8 Nov
4.94 out of 5 average rating, 47 reviews
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Home in Gloucester
Luxury Townhouse in Downtown with Free Parking #2
3 bedrooms, 3 beds
16–21 Nov
4.94 out of 5 average rating, 89 reviews
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Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
2–7 Nov
4.98 out of 5 average rating, 99 reviews
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Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Home in Gloucester
Panoramic Ocean View; walk to private beach
5 bedrooms, 8 beds
11–16 Oct
4.96 out of 5 average rating, 91 reviews
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Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 140 reviews
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Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 94 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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Home in Gloucester
Gloucester Ocean View Home
4 bedrooms, 7 beds
22–27 Sept
4.94 out of 5 average rating, 16 reviews
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Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
12–17 Oct
4.96 out of 5 average rating, 45 reviews
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Flat in Gloucester
Charming 2BR•Walk to Harbor & Downtown•Close2Salem
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds
15–20 Nov
4.97 out of 5 average rating, 36 reviews
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Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds
3–8 Oct
4.9 out of 5 average rating, 51 reviews