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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Harbor View Walk to Beach & Town, 6Guests KingBeds
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Aug
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4.97 out of 5 average rating, 151 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 beds, 2 bathrooms
27 Aug – 1 Sept
Superhost
Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
Guest favourite
Home in Gloucester
Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!
4.93 out of 5 average rating, 112 reviews, 2 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
4.92 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
Top guest favourite
Flat in Gloucester
Blue Magnolia
5.0 out of 5 average rating, 79 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4.84 out of 5 average rating, 219 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Holiday home in Gloucester
On the Water Gem - 2 BR -The Cove Lanesville
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
4.94 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
4.97 out of 5 average rating, 362 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Gloucester
Parsons at Stage Fort
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
Top guest favourite
Flat in Rockport
Fall Asleep to Waves — Steps to Shops & Dining
4.93 out of 5 average rating, 71 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Gloucester
Boulevard Retreat
4.99 out of 5 average rating, 128 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Gloucester
Evensong: Lovely Oceanview Retreat with Dock
4.95 out of 5 average rating, 42 reviews, 3 bedrooms, 6 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
4.93 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov