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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
17–22 Aug
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4.97 out of 5 average rating, 156 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, 83 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 109 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 42 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 97 reviews
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 31 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, 15 reviews
Top guest favourite
Home in Gloucester
Harbor House with Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 58 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 154 reviews
Guest favourite
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Gloucester
The Beach House on the Boulevard Ocean Front!
5 bedrooms, 18 beds, 2.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Home in Rockport
Oceanfront Home Rockport
5 bedrooms, 10 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 39 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
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, 13 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 86 reviews