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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Home in Gloucester
Waterfront Rocky Neck Cottage | Gloucester Harbor
3 bedrooms, 4 beds, 1 private bathroom
3–8 Nov
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4.93 out of 5 average rating, 193 reviews
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Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.97 out of 5 average rating, 149 reviews
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Top guest favourite
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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Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
14–19 Nov
4.96 out of 5 average rating, 162 reviews
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Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
20–25 Nov
4.99 out of 5 average rating, 93 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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Guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.91 out of 5 average rating, 291 reviews
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Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 104 reviews
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Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 95 reviews
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Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.89 out of 5 average rating, 44 reviews
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
3–8 Oct
4.9 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.93 out of 5 average rating, 15 reviews
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Guest house in Rockport
Historic Carriage House | Dog Friendly | Hot Tub
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.99 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 62 reviews
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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
6 bedrooms, 10 beds, 4.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
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, 114 reviews
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Guest favourite
Home in Gloucester
Pavilion Beach Townhouse
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 76 reviews
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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
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