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Search results; Over 1,000 homes in Gloucester

Top guest favorite
This artist-renovated Annisquam cottage surrounds you with gardens and water on 3 sides
1 bedroom, 1 bed, 1 private bath
Nov 2 – 7
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4.96 out of 5 average rating, 309 reviews
Superhost
Look out over the Atlantic from this newly renovated Magnolia Beach apartment
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 27 – Sep 1
Top guest favorite
Wake to open ocean views from your deck at this Folly Cove apartment
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 20 – 25
Top guest favorite
Watch sunsets over Ipswich Bay from the decks of this Lanesville waterfront home
4.99 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 13 – 18
Top guest favorite
This Queen Anne Victorian suite on Governor’s Hill gives you coastal Gloucester charm
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 1 bed, 1 bath
Nov 2 – 7
Top guest favorite
This Gloucester apartment gives you a fenced yard with a fire pit and BBQ
4.93 out of 5 average rating, 127 reviews, 2 bedrooms, 2 beds, 1 bath
Dec 4 – 9
Top guest favorite
Ocean views greet you at this contemporary Gloucester house near Good Harbor Beach
4.95 out of 5 average rating, 42 reviews, 4 bedrooms, 6 beds, 3 baths
Sep 12 – 17
Top guest favorite
This restored East Gloucester cottage gives you a stone patio and private backyard
5.0 out of 5 average rating, 32 reviews, 1 bedroom, 2 beds, 1 bath
Sep 7 – 12
Top guest favorite
This Gloucester townhouse puts you on the estuary with a fire pit and patio
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
Top guest favorite
This newly renovated Rockport condo gives you a private patio facing the harbor
5.0 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bath
Nov 9 – 14
Top guest favorite
This light-filled 1846 Rockport home puts you a short walk from the beach
4.97 out of 5 average rating, 367 reviews, 4 bedrooms, 6 beds, 1.5 baths
Sep 13 – 18
Top guest favorite
Ocean views greet you at this Lanesville suite, a 5-minute walk from the beach
4.98 out of 5 average rating, 167 reviews, 1 bedroom, 1 bed, 2 baths
Oct 3 – 8
Guest favorite
Local art fills this Gloucester apartment, a mile from Good Harbor Beach
4.93 out of 5 average rating, 28 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Top guest favorite
Take in ocean sunsets by the gas fireplace at this Gloucester house on Lane’s Cove
4.93 out of 5 average rating, 45 reviews, 2 bedrooms, 2 beds, 1.5 baths
Nov 8 – 13
Top guest favorite
Watch fishing boats return from the sunroom of this Gloucester harbor house
4.98 out of 5 average rating, 98 reviews, 3 bedrooms, 4 beds, 2.5 baths
Aug 29 – Sep 3
Top guest favorite
This ultra-contemporary Manchester-by-the-Sea villa gives you 20 secluded acres of forest
4.97 out of 5 average rating, 73 reviews, 10 bedrooms, 15 beds, 3 baths
Aug 16 – 22
Top guest favorite
This freshly refurbished waterfront Rockport condo puts you near Bearskin Neck
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bath
Nov 21 – 26
Guest favorite
This newly renovated Gloucester condo puts you just off Main St
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
This hand-built Rockport cabin puts you deep in 2,500 acres of woodland
4.97 out of 5 average rating, 497 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 7 – 12