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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4 bedrooms, 4 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.99 out of 5 average rating, 223 reviews
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Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 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
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, 249 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 89 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 281 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
16–21 Aug
4.96 out of 5 average rating, 45 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
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
Guest favourite
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 9 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
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
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
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
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
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
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
4–9 Dec
4.98 out of 5 average rating, 178 reviews