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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
17–22 Oct
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4.92 out of 5 average rating, 241 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
4.98 out of 5 average rating, 172 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, 9 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Gloucester
Walk to Good Harbor Beach
4.93 out of 5 average rating, 131 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
4.92 out of 5 average rating, 12 reviews, 2 bedrooms, 6 beds, 1 bathroom
30 Aug – 4 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
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 121 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Flat in Gloucester
Charming Retreat / Close to Beaches
4.93 out of 5 average rating, 122 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
Top guest favourite
Apartment in Gloucester
Smith Cove Cottage Condo
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Rockport
Oceanfront Rockport Getaway with Loft & Views
4.99 out of 5 average rating, 82 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
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
Top guest favourite
Guest house in Rockport
Gingerbread House | Hot Tub | Dog Friendly
4.99 out of 5 average rating, 158 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4.99 out of 5 average rating, 220 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–25 Jul
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
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
5.0 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
Superhost
Flat in Rockport
Garden Getaway
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul