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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 private bathroom
6–11 Nov
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4.92 out of 5 average rating, 119 reviews
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Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.97 out of 5 average rating, 149 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, 28 reviews
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Top guest favourite
Home in Gloucester
Ocean views! Welcome to Sea Breeze! Winter rates!
4 bedrooms, 4 beds, 2.5 bathrooms
3–8 Nov
4.98 out of 5 average rating, 114 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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Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Nov
4.98 out of 5 average rating, 99 reviews
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Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
20–25 Nov
4.99 out of 5 average rating, 92 reviews
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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.93 out of 5 average rating, 14 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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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, 47 reviews
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Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 104 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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Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Flat in Gloucester
Charming 2BR•Walk to Harbor & Downtown•Close2Salem
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 38 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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Top guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
14–19 Nov
4.95 out of 5 average rating, 19 reviews
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Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 62 reviews
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Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Nov
4.99 out of 5 average rating, 86 reviews
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Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 94 reviews