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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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Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.97 out of 5 average rating, 149 reviews
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Top guest favourite
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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Top guest favourite
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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Top guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
14–19 Nov
4.95 out of 5 average rating, 19 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds
3–8 Nov
4.98 out of 5 average rating, 114 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 favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds
1–6 Nov
4.91 out of 5 average rating, 289 reviews
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Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds
8–13 Nov
4.93 out of 5 average rating, 46 reviews
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Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds
14–19 Nov
4.96 out of 5 average rating, 162 reviews
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Home in Annisquam
Hide & Seek
4 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds
1–6 Nov
4.93 out of 5 average rating, 14 reviews
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Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds
19–24 Sept
4.8 out of 5 average rating, 282 reviews
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Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds
6–11 Nov
4.99 out of 5 average rating, 87 reviews
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Guest favourite
Flat in Rockport
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds
25–30 Oct
4.88 out of 5 average rating, 155 reviews
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Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds
2–7 Nov
4.96 out of 5 average rating, 50 reviews
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Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds
3–8 Nov
4.97 out of 5 average rating, 77 reviews