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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest suite in Gloucester
Welcoming, Quiet Gloucester Space
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.91 out of 5 average rating, 115 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 83 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Home in Essex
Home in Essex
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Rockport
Oceanfront Retreat w/ Deck & Parking
2 bedrooms, 4 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 88 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 8 reviews
Home in Gloucester
Hide & Seek
4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
New place to stay
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Rockport
Downtown Rockport Stay with Private Ocean Deck
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 64 reviews
Top guest favourite
Home in Gloucester
Lovely home by the sea!
3 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Gloucester
Stroll to SeaView/Beach; Great Yard
4 bedrooms, 6 beds, 1.5 bathrooms
28 Aug – 2 Sept
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
17–22 Nov
4.97 out of 5 average rating, 144 reviews
Guest favourite
Flat in Gloucester
Long Beach Suites: Steps Away From Surf!
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.89 out of 5 average rating, 148 reviews
Top guest favourite
Apartment in Gloucester
3BR Oceanfront Condo with decks
3 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 161 reviews