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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
Ocean House Hotel at Bass Rocks, Deluxe two queen.
1 bedroom, 2 queen beds
25–30 Oct
New place to stay
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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds
2–7 Nov
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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, 28 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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Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds
1–6 Oct
4.96 out of 5 average rating, 152 reviews
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Top guest favourite
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds
3–8 Nov
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Gloucester
Charming 2BR•Walk to Harbor & Downtown•Close2Salem
2 bedrooms, 2 beds
8–13 Nov
4.98 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds
13–18 Nov
4.99 out of 5 average rating, 89 reviews
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Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds
6–11 Dec
4.97 out of 5 average rating, 149 reviews
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Top guest favourite
Home in Gloucester
Panoramic Ocean View; walk to private beach
5 bedrooms, 8 beds
11–16 Oct
4.96 out of 5 average rating, 91 reviews
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Top guest favourite
Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed
18–23 Oct
4.87 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds
3–8 Nov
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 16 reviews
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Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds
8–13 Nov
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Gloucester
Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem
3 bedrooms, 4 beds
9–14 Nov
4.98 out of 5 average rating, 105 reviews