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Search results; Over 1,000 homes in Gloucester

Guest favourite
Flat in Gloucester
Amazing Ocean View In-Law Apt.
1 bedroom, 2 beds, 1 private bathroom
1–6 Nov
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4.86 out of 5 average rating, 138 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
2–7 Nov
5.0 out of 5 average rating, 4 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, 172 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
Flat in Gloucester
Charming Retreat / Close to Beaches
2 bedrooms, 2 beds
3–8 Oct
4.93 out of 5 average rating, 122 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 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, 52 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 7 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, 243 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
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds
30 Aug – 4 Sept
4.92 out of 5 average rating, 12 reviews
Guest favourite
Flat in Gloucester
Artist Retreat
1 bedroom, 1 king bed
13–18 Jul
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds
26–31 Aug
4.91 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 122 reviews
Superhost
Flat in Rockport
Garden Getaway
1 bedroom, 1 bed
24–29 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
2 bedrooms, 4 beds
16–21 Nov
4.99 out of 5 average rating, 82 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, 158 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds
12–17 Jul
4.94 out of 5 average rating, 77 reviews