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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, 319 reviews
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Featured hotel
Hotel in Gloucester
Deluxe two queens - ground level
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
New place to stay
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.94 out of 5 average rating, 48 reviews
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Superhost
Home in Gloucester
Stay in Central Gloucester
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Nov
New place to stay
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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 10 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
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 65 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, 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, 3 bathrooms
12–17 Oct
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
14–19 Nov
4.96 out of 5 average rating, 162 reviews
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Top guest favourite
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
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, 1 bathroom
8–13 Nov
4.99 out of 5 average rating, 176 reviews
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Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
New place to stay
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Guest favourite
Loft in Gloucester
Gloucester Large 2-Room Studio, Full Kitchen, Deck
1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Rockport
Harbor Views in the Heart of Rockport
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 69 reviews
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Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
20–25 Nov
4.99 out of 5 average rating, 93 reviews