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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
,
4.92 out of 5 average rating, 257 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds
20–25 Sept
New place to stay
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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, 27 reviews
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Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 65 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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Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
17–22 Sept
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Gloucester
Cozy Coastal Cape Ann Suite - Minutes to Beaches
2 bedrooms, 6 beds
15–20 Nov
4.97 out of 5 average rating, 35 reviews
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Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds
10–15 Nov
4.99 out of 5 average rating, 165 reviews
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Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
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
11–16 Nov
4.99 out of 5 average rating, 89 reviews
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Guest favourite
Home in Gloucester
PVT Waterfront Deck•Firepit•Parking•Close to Salem
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.9 out of 5 average rating, 51 reviews
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Top guest favourite
Guest house in Rockport
Sea Mist Cottage Rockport, MA
1 queen bed
1–6 Nov
5.0 out of 5 average rating, 271 reviews
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Top guest favourite
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed
18–23 Sept
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Guest house in Rockport
Historic Carriage House | Dog Friendly | Hot Tub
1 bedroom, 2 beds
2–7 Nov
4.99 out of 5 average rating, 174 reviews
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Guest favourite
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Flat in Rockport
Downtown Rockport Stay with Private Ocean Deck
1 bedroom, 1 bed
1–6 Nov
4.93 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
6 bedrooms, 9 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 58 reviews