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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
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4.97 out of 5 average rating, 318 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, 99 reviews
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Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
11–16 Nov
4.99 out of 5 average rating, 89 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 94 reviews
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Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.96 out of 5 average rating, 50 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 28 reviews
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Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 110 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 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 Oct
4.96 out of 5 average rating, 45 reviews
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Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Nov
4.99 out of 5 average rating, 88 reviews
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Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.98 out of 5 average rating, 765 reviews
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Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 43 reviews
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Cottage in Rockport
Oceanfront Cottage on Long Beach - Rockport, MA
4 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 38 reviews
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Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 37 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, 10 reviews
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Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.94 out of 5 average rating, 47 reviews
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Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 7 reviews