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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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Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
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Top guest favourite
Flat in Gloucester
Stony Brook: Woodsy setting, secluded
1 bed, 1 bathroom
18–23 Oct
4.87 out of 5 average rating, 46 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
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 65 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
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
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
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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Guest favourite
Home in Gloucester
360 degree view of the Annisquam river and Ocean
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 12 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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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
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Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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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Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Heart of Rockport
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.94 out of 5 average rating, 79 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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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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Guest favourite
Home in Gloucester
Views of Lobster Cove AirBnB fees included in rate
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 145 reviews
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Top guest favourite
Home in Gloucester
Panoramic Ocean View; walk to private beach
5 bedrooms, 8 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 91 reviews