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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, 255 reviews
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Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
17–22 Nov
4.97 out of 5 average rating, 147 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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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
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.91 out of 5 average rating, 11 reviews
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Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 59 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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Guest favourite
Flat in Gloucester
Stay at the Marina (Gloucester)
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 134 reviews
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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 21 reviews
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Flat in Rockport
4 Bed Water View w/ Parking
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.99 out of 5 average rating, 173 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 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
Gloucester Ocean View Home
4 bedrooms, 7 beds, 3 bathrooms
9–14 Sept
4.94 out of 5 average rating, 16 reviews
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Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 57 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
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Top guest favourite
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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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
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 64 reviews