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
28 Aug – 2 Sept
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4.93 out of 5 average rating, 183 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
New place to stay, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 6 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 168 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
4.98 out of 5 average rating, 51 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 119 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
4.92 out of 5 average rating, 272 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
4.99 out of 5 average rating, 135 reviews, 5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
5.0 out of 5 average rating, 103 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
Top guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
4.99 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
22–29 Aug
Guest favourite
Apartment in Gloucester
Retreat to tranquility - water views
4.95 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Apartment in Rockport
Waterfront Downtown Apartment • Walk Everywhere
4.95 out of 5 average rating, 117 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Sept
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
4.97 out of 5 average rating, 149 reviews, 1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
4.99 out of 5 average rating, 155 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 79 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
4.91 out of 5 average rating, 34 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Aug