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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Plum Cove Cottage with king suite!
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
,
4.93 out of 5 average rating, 121 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
12–17 Sept
New place to stay
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Gloucester
Walk to Good Harbor Beach
1 bedroom, 2 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 131 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds
1–6 Nov
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed
17–22 Oct
4.92 out of 5 average rating, 240 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
1 bedroom, 2 queen beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 51 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Gloucester
Cozy Apartment at Green Landing, No Cleaning Fee
1 bedroom, 1 queen bed
19–24 Jul
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
2 bedrooms, 3 beds
22–29 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds
9–14 Nov
5.0 out of 5 average rating, 105 reviews
Superhost
Flat in Rockport
Garden Getaway
1 bedroom, 1 bed
14–19 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in Gloucester
3BR Harborside Home|Gloucester+Rockport|Ocean View
3 bedrooms, 3 queen beds
16–21 Sept
4.97 out of 5 average rating, 88 reviews
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
1 bedroom, 3 beds
4–9 Sept
4.96 out of 5 average rating, 220 reviews
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
1 bedroom, 2 beds
13–18 Sept
4.99 out of 5 average rating, 156 reviews