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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
Top guest favourite
Rooms in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 280 reviews
Guest favourite
Flat in Gloucester
Artist Retreat
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 27 reviews
Guest favourite
Flat in Gloucester
Chic Gloucester Escape~Walk 2 ShopsHarbor&Dining
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 22 reviews
Flat in Gloucester
Rocky Neck Hideaway on Wonson Cove
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
1 bedroom, 1 queen bed, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Room in Gloucester
Suite Magnolia
1 king bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 114 reviews
Top guest favourite
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Gloucester
Boho Beach Condo for Ocean Escape
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 138 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
4.92 out of 5 average rating, 36 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
4.88 out of 5 average rating, 144 reviews
Guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 9 reviews
Guest favourite
Guest suite in Gloucester
Beachside~at Good Harbor Beach 2 person 1 bedroom.
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Gloucester
Seaside Suite
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 10 reviews