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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
17–22 Oct
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4.92 out of 5 average rating, 239 reviews
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, 6 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 6 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, 8 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Annisquam
Panoramic Ocean View; walk to private beach
5 bedrooms, 8 beds, 2 bathrooms
28 Aug – 2 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Gloucester
Charming 2BR Gem • Walk to Harbor & Downtown
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 21 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
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Gloucester
New England Coastal Residence
4 bedrooms, 7 beds, 2 bathrooms
13–18 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
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
New place to stay
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
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, 94 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, 24 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.89 out of 5 average rating, 38 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