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
12–17 Sept
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, 169 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
8–13 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, 275 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
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
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
4.99 out of 5 average rating, 156 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Guest house in Rockport
Seagull’s Nest
5.0 out of 5 average rating, 50 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 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
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
Guest suite in Rockport
Historic Rockport Large Suite, Entire Third Floor.
4.99 out of 5 average rating, 153 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
4.96 out of 5 average rating, 219 reviews, 1 bedroom, 3 beds, 1 bathroom
14–19 Aug
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
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
Top guest favourite
Cottage in Gloucester
Shore Cottage • Peaceful Coastal Retreat
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul