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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
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
27 Aug – 1 Sept
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 81 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds
27 Aug – 1 Sept
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 95 reviews
Top guest favourite
Home in Gloucester
The Beach House on the Boulevard Ocean Front!
5 bedrooms, 18 beds
24–29 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 84 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.93 out of 5 average rating, 71 reviews
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds
16–21 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 128 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds
3–8 Aug
4.94 out of 5 average rating, 78 reviews
Top guest favourite
Townhouse in Gloucester
Luxury Portside Townhome Steps to Niles Beach
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Townhouse in Gloucester
Between 2 Beaches
3 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 197 reviews