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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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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, 27 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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Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
New place to stay
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Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Nov
4.93 out of 5 average rating, 46 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, 289 reviews
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Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
18–23 Sept
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 110 reviews
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Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
11–16 Nov
4.99 out of 5 average rating, 89 reviews
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Top guest favourite
Guest house in Rockport
Sea Mist Cottage Rockport, MA
1 queen bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 271 reviews
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Guest favourite
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.93 out of 5 average rating, 14 reviews
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Superhost
Home in Gloucester
Stay at Windward Point
4 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 reviews