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Search results; Over 1,000 homes in Gloucester

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Guest favourite
Cottage in Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
4 bedrooms, 6 beds, 2 private bathrooms
4–9 Oct
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4.86 out of 5 average rating, 193 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
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
Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed, 1 bathroom
16–21 Oct
4.87 out of 5 average rating, 46 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
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 152 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, 28 reviews
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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
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, 32 reviews
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Guest favourite
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Gloucester
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Nov
4.99 out of 5 average rating, 88 reviews
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Top guest favourite
Flat in Gloucester
Charming 2BR•Walk to Harbor & Downtown•Close2Salem
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 39 reviews
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Hotel in Gloucester
Ocean House Hotel - Premium King
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
4.75 out of 5 average rating, 20 reviews
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Guest favourite
Home in Gloucester
River's Edge Cottage Gloucester
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Flat in Gloucester
Annisquam Village Abode - access to private beach
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 107 reviews
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Top guest favourite
Apartment in Gloucester
KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 206 reviews
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Top guest favourite
Guest suite in Rockport
Historic Rockport Large Suite, Entire Third Floor.
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 164 reviews
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Guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds, 1 bathroom
3–8 Nov
4.95 out of 5 average rating, 234 reviews
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Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 19 reviews