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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
29 Aug – 3 Sept
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4.93 out of 5 average rating, 187 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 277 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Nov
Guest favourite
Home in Gloucester
Parsons at Stage Fort
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Superhost
Flat in Gloucester
Chic Gloucester Escape~Walk 2 ShopsHarbor&Dining
4.89 out of 5 average rating, 19 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Room in Gloucester
Spacious Private Suite w/ Bath in Lanesville
New place to stay, 1 queen bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
4.99 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 139 reviews, 5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
4.99 out of 5 average rating, 84 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
4.92 out of 5 average rating, 245 reviews, 1 bed, 1 bathroom
4–9 Apr
Top guest favourite
Cottage in Rockport
Cozy Oceanfront Beach Cottage - Walk to Downtown
4.96 out of 5 average rating, 27 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Apartment in Gloucester
IDEAL Location/River & Harbor Views/Beach/Town
5.0 out of 5 average rating, 39 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Room in Gloucester
Suite Magnolia
5.0 out of 5 average rating, 60 reviews, 1 king bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
4.93 out of 5 average rating, 126 reviews, 2 bedrooms, 2 beds, 1 bathroom
4–9 Dec
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Oct
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
4.93 out of 5 average rating, 71 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Gloucester
Private Beachfront Property in Gloucester
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Nov
Top guest favourite
Guest house in Rockport
Seagull’s Nest
5.0 out of 5 average rating, 54 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept