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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 bedrooms, 4 beds, 1 private bathroom
29 Aug – 3 Sept
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4.93 out of 5 average rating, 187 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
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Home in Ipswich
Direct Waterfront on Plum Island Sound Sunsets
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
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Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 78 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, 77 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, 9 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, 32 reviews
Top guest favourite
Home in Gloucester
Seaside Escape
2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 54 reviews
Superhost
Home in Rockport
Waterfront Retreat at Motif Annex
1 bedroom, 2 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 4 reviews
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
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
Top guest favourite
Home in Gloucester
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 47 reviews
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Guest suite in Gloucester
A charming Entire Guest Suite in Gloucester
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Home in Gloucester
“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor
4 bedrooms, 6 beds, 3 bathrooms
26–31 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Home in Gloucester
Rocky Neck Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
26–31 Aug
4.99 out of 5 average rating, 221 reviews
Guest favourite
Home in Gloucester
PVT Waterfront Deck|Firepit|Workspace|Free Parking
3 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.9 out of 5 average rating, 41 reviews
Top guest favourite
Home in Gloucester
Lane's Cove Bijou
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.93 out of 5 average rating, 44 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
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