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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest suite in Gloucester
Quirky room above convenience store, near water.
1 bedroom, 1 bed, 1 private bathroom
31 Dec – 5 Jan
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4.75 out of 5 average rating, 483 reviews
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 bed, 1 bathroom
11–16 Jul
New place to stay
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 168 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest suite in Gloucester
Beachside~at Good Harbor Beach 2 person 1 bedroom.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 21 reviews
Home in Gloucester
ABC Beach House
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 25 reviews
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
New place to stay
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
9–14 Jul
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in Rockport
Sea Vagabond - Watch the waves, stroll to the sand
4 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
4.81 out of 5 average rating, 93 reviews
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Gloucester
The Beach House on the Boulevard Ocean Front!
5 bedrooms, 18 beds, 2.5 bathrooms
25–30 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Gloucester
Private Beach!
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Gloucester
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 31 reviews