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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
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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Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 27 reviews
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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 Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 140 reviews
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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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Flat in Gloucester
The Gilbert: 1-Bed downtown suite, walk to beach.
1 bedroom, 1 king bed, 1 bathroom
1–6 Mar
4.96 out of 5 average rating, 192 reviews
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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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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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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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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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Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds, 1.5 bathrooms
19–24 Sept
4.8 out of 5 average rating, 282 reviews
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Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
14–19 Nov
5.0 out of 5 average rating, 18 reviews
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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
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Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
18–23 Sept
4.96 out of 5 average rating, 45 reviews
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Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.88 out of 5 average rating, 43 reviews
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Bungalow in Gloucester
Mermaid Surf Bungalow on Good Harbor Beach
3 bedrooms, 5 beds, 2 bathrooms
3–8 Nov
4.97 out of 5 average rating, 77 reviews
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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