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Search results; Over 1,000 homes in Gloucester

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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4.96 out of 5 average rating, 308 reviews
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 278 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Guest favourite
Flat in Gloucester
Chic Gloucester Escape~Walk 2 ShopsHarbor&Dining
4.9 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Gloucester
Walk to DNTN~Beach~Beauport~Boat Island~New Home
4.98 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 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
Top guest favourite
Flat in Gloucester
Ocean View | Walk to Downtown & Beach | Skylight
4.98 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Nov
Top guest favourite
Room in Gloucester
Suite Magnolia
5.0 out of 5 average rating, 63 reviews, 1 king bed, 1 bathroom
2–7 Aug
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
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 140 reviews, 5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
Top guest favourite
Cottage in Gloucester
Shore Cottage • Peaceful Coastal Retreat
5.0 out of 5 average rating, 46 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest house in Rockport
Seagull’s Nest
5.0 out of 5 average rating, 55 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Flat in Gloucester
Captain's Lookout | Roof Deck & Harbor Views
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
4.96 out of 5 average rating, 153 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Rockport
Oceanfront Stay w/ Deck & Parking
4.99 out of 5 average rating, 85 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
Top guest favourite
Flat in Gloucester
Seaside Suite
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
4.92 out of 5 average rating, 246 reviews, 1 bed, 1 bathroom
4–9 Apr