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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
,
4.96 out of 5 average rating, 308 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 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, 79 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
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
4.99 out of 5 average rating, 84 reviews
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Salem
2-Bedroom Ocean View Walk to Beach and Downtown
2 bedrooms, 4 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 154 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.94 out of 5 average rating, 78 reviews
Top guest favourite
Home in Gloucester
The Beach House on the Boulevard Ocean Front!
5 bedrooms, 18 beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 41 reviews
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, 36 reviews
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 71 reviews
Guest favourite
Home in Gloucester
Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.93 out of 5 average rating, 112 reviews
Guest favourite
Flat in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
2 bedrooms, 5 beds, 1.5 bathrooms
10–15 Aug
4.79 out of 5 average rating, 273 reviews
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.84 out of 5 average rating, 219 reviews