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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
,
4.96 out of 5 average rating, 308 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, 280 reviews
Guest favourite
Room in Ipswich
Cedarwood Farm - Marie Antoinette Suite
1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 45 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
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
Cabin in Beverly
Garden School Cabin
2 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 3 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, 86 reviews
Guest favourite
Home in Gloucester
The Essex of Gloucester
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 86 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
Guest favourite
Flat in Rockport
Apartment in Rockport
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest suite in Newbury
Parker River House Two Bedroom
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 90 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, 364 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
Tiny home in Gloucester
Smith Cove Cottgage
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Cabin in Rockport
The Solar Powered Dogtown Cabin at Applecart Farm
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 497 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
7–12 Aug
New place to stay
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 138 reviews