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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 private bathroom
1–6 Nov
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4.86 out of 5 average rating, 138 reviews
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Featured hotel
Hotel in Gloucester
Ocean House Hotel at Bass Rocks, Deluxe two queen.
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
New place to stay
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Guest favourite
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, 150 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, 29 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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Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
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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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 16 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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Top guest favourite
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, 177 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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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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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, 48 reviews
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.91 out of 5 average rating, 53 reviews
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Guest favourite
Loft in Gloucester
Gloucester Large 2-Room Studio, Full Kitchen, Deck
1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 7 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, 115 reviews
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Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.88 out of 5 average rating, 156 reviews
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Top guest favourite
Flat in Gloucester
Stay at the Marina
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 11 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