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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
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed
1–6 Nov
4.87 out of 5 average rating, 46 reviews
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Apartment in Rockport
Widows Bay Rockport Apt • Train To Salem
1 bedroom, 3 beds
9–14 Oct
4.95 out of 5 average rating, 130 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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Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 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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Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 65 reviews
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Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
11–16 Nov
4.99 out of 5 average rating, 89 reviews
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Guest house in Rockport
Historic Carriage House | Dog Friendly | Hot Tub
1 bedroom, 2 beds
2–7 Nov
4.99 out of 5 average rating, 175 reviews
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Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds
20–25 Sept
New place to stay
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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
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
“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 Rockport
Harbor Views in the Heart of Rockport
1 bedroom, 1 bed
1–6 Nov
4.93 out of 5 average rating, 68 reviews
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Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
4–9 Oct
5.0 out of 5 average rating, 37 reviews
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Guest favourite
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
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds
3–8 Nov
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 58 reviews