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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
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4.97 out of 5 average rating, 318 reviews
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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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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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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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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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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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
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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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 Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds
19–24 Sept
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
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
4–9 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
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
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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
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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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
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds
15–20 Nov
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Flat in Rockport
Harbor Views in the Heart of Rockport
1 bedroom, 1 bed
1–6 Nov
4.93 out of 5 average rating, 68 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