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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
2 bedrooms, 3 beds, 1 private bathroom
9–14 Jul
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4.97 out of 5 average rating, 155 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
4.92 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
4.79 out of 5 average rating, 273 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
10–15 Aug
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Gloucester
Lovely home by the sea!
4.95 out of 5 average rating, 19 reviews, 3 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
Guest favourite
Home in Gloucester
Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!
4.93 out of 5 average rating, 112 reviews, 2 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 219 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 79 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 11 reviews, 2 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, 44 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
4.93 out of 5 average rating, 71 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
5.0 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Aug
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 128 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept