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Search results; Over 1,000 homes in Gloucester

Top guest favorite
Loft in Gloucester
Pine-paneled loft with 3 skylights
Studio, 1 bed, 1 private bath
Apr 4 – 9
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4.92 out of 5 average rating, 250 reviews
Superhost
Apartment in Gloucester
Ocean views near Magnolia Beach
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 27 – Sep 1
Top guest favorite
Apartment in Gloucester
Yard ends at the ocean, Folly Cove
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 20 – 25
Top guest favorite
Vacation home in Gloucester
Waterfront with sunset decks on Ipswich Bay
4.99 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 13 – 18
Top guest favorite
Guest suite in Gloucester
Victorian suite near Gloucester’s waterfront
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 1 bed, 1 bath
Nov 2 – 7
Top guest favorite
Apartment in Gloucester
Fenced yard with a fire pit, near beach
4.93 out of 5 average rating, 127 reviews, 2 bedrooms, 2 beds, 1 bath
Dec 4 – 9
Top guest favorite
Home in Gloucester
Ocean views 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
Tiny home in Gloucester
Restored cottage near Rocky Neck Art Colony
5.0 out of 5 average rating, 32 reviews, 1 bedroom, 2 beds, 1 bath
Sep 7 – 12
Top guest favorite
Townhouse in Gloucester
On the estuary, 4 minutes to beach
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
Top guest favorite
Condo in Rockport
Newly renovated, across from Rockport Harbor
5.0 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bath
Nov 9 – 14
Top guest favorite
Home in Rockport
Light-filled 1846 home near the beach
4.97 out of 5 average rating, 367 reviews, 4 bedrooms, 6 beds, 1.5 baths
Sep 13 – 18
Top guest favorite
Guest suite in Gloucester
Ocean views, 5-minute walk to beach
4.98 out of 5 average rating, 167 reviews, 1 bedroom, 1 bed, 2 baths
Oct 3 – 8
Guest favorite
Apartment in Gloucester
Local art, a mile from the beach
4.93 out of 5 average rating, 28 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Top guest favorite
Home in Gloucester
Clawfoot tub with cove views, gas fireplace
4.93 out of 5 average rating, 45 reviews, 2 bedrooms, 2 beds, 1.5 baths
Nov 8 – 13
Top guest favorite
Home in Gloucester
Harbor views from the sunroom and deck
4.98 out of 5 average rating, 98 reviews, 3 bedrooms, 4 beds, 2.5 baths
Aug 29 – Sep 3
Top guest favorite
Villa in Manchester-by-the-Sea
Farnsworth-inspired retreat on 20 private acres
4.97 out of 5 average rating, 73 reviews, 10 bedrooms, 15 beds, 3 baths
Aug 16 – 22
Top guest favorite
Apartment in Rockport
Waterfront condo near Bearskin Neck
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bath
Nov 21 – 26
Guest favorite
Apartment in Gloucester
Newly renovated, blocks from the beach
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Cabin in Rockport
Hand-built cabin in 2,500 acres of woods
4.97 out of 5 average rating, 497 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 7 – 12