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Search results; Over 1,000 homes in Gloucester

Bed and breakfast in Massachusetts
Comfortable First Floor Room, Walk to Rocky Coast
1 bedroom, 1 bed, 1 private bathroom
4–9 Jul
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4.88 out of 5 average rating, 69 reviews
Home in Massachusetts
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, 6 reviews
Guest suite in Massachusetts
Herringbone Suite at Beacon House
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
New place to stay
Home in Massachusetts
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 10 reviews
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 95 reviews
Home in Massachusetts
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 4 reviews
Flat in Massachusetts
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 6 reviews
Flat in Massachusetts
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 168 reviews
Flat in Massachusetts
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
Home in Massachusetts
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
Flat in Massachusetts
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 16 reviews
Townhouse in Massachusetts
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 Massachusetts
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
New place to stay
Home in Massachusetts
ABC Beach House
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
New place to stay
Home in Massachusetts
The Mariner|Family Friendly|Backyard|Walk 2 Beach
3 bedrooms, 5 beds, 2.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 84 reviews
Home in Massachusetts
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
Home in Massachusetts
Private Pickleball | Family Friendly | Sleep 18
6 bedrooms, 12 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Home in Massachusetts
Private Beach!
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
4.96 out of 5 average rating, 50 reviews
Cottage in Massachusetts
Sunny & private cottage in Lanesville Village
2 bedrooms, 3 beds, 1 bathroom
7–12 Feb
4.97 out of 5 average rating, 152 reviews