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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
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4.92 out of 5 average rating, 280 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed, 1 bathroom
4–9 Apr
4.92 out of 5 average rating, 248 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 86 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 87 reviews
Guest favourite
Flat in Beverly
Cozy Boho Den
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Room in Ipswich
Cedarwood Farm - Marie Antoinette Suite
1 queen bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Apartment in Rockport
Waterfront Downtown Apartment • Walk Everywhere
1 bedroom, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 124 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Room in Gloucester
The William Haskell House N. Ell
1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4 bedrooms, 6 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 366 reviews
Top guest favourite
Townhouse in Gloucester
The Haabah Beach Retreat—4 Minute Walk to Beach
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
1 bedroom, 1 queen bed, 1 bathroom
7–12 Nov
4.98 out of 5 average rating, 757 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 88 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
2 bedrooms, 2 beds, 1 bathroom
4–9 Dec
4.93 out of 5 average rating, 127 reviews
Guest favourite
Loft in Gloucester
Gloucester Large 2-Room Studio, Full Kitchen, Deck
1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews