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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, 257 reviews
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Featured hotel
Hotel in Gloucester
Ocean House Hotel at Bass Rocks, Deluxe two queen.
1 bedroom, 2 queen beds
25–30 Oct
New place to stay
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
3–8 Nov
4.94 out of 5 average rating, 47 reviews
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Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 29 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 house in Rockport
Seagull’s Nest
1 bedroom, 2 beds
8–13 Nov
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds
13–18 Nov
4.99 out of 5 average rating, 89 reviews
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Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds
18–23 Oct
New place to stay
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Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Guest house in Rockport
Historic Carriage House | Dog Friendly | Hot Tub
1 bedroom, 2 beds
8–13 Nov
4.99 out of 5 average rating, 176 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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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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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds
20–25 Nov
4.99 out of 5 average rating, 93 reviews
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Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds
8–13 Nov
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Gloucester
House on tidal river, spacious deck, private yard
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 17 reviews