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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
4–9 Apr
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4.92 out of 5 average rating, 245 reviews
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds
27 Aug – 1 Sept
4.95 out of 5 average rating, 41 reviews
Superhost
Flat in Gloucester
Stunning Ocean-View Retreat, Magnolia Beach
2 bedrooms, 2 king beds
27 Aug – 1 Sept
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Gloucester
Blue Magnolia
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 79 reviews
Guest favourite
Home in Gloucester
Parsons at Stage Fort
3 bedrooms, 4 beds
7–12 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Guest suite in Gloucester
Herringbone Suite at Beacon House
1 bedroom, 1 king bed
2–7 Nov
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Gloucester
Private Beachfront Property in Gloucester
3 bedrooms, 3 beds
4–9 Nov
5.0 out of 5 average rating, 9 reviews
Guest favourite
Place to stay in Gloucester
Back Shore Hidden Garden Suite
3 bedrooms, 3 beds
3–8 Aug
4.94 out of 5 average rating, 77 reviews
Guest favourite
Home in Gloucester
Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!
2 bedrooms, 5 beds
1–6 Nov
4.93 out of 5 average rating, 112 reviews
Superhost
Home in Gloucester
Stay at Wingaersheek
3 bedrooms, 5 beds
7–12 Sept
New place to stay
Top guest favourite
Flat in Gloucester
Ocean View | Walk to Downtown & Beach | Skylight
1 bedroom, 2 beds
2–7 Aug
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Townhouse in Gloucester
Oceanview 3BR Townhouse | Steps to Downtown
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds
14–19 Nov
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Home in Annisquam
Annisquam Getaway - Water View+Walk To The Beach
3 bedrooms, 5 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
4 bedrooms, 5 beds
23–28 Aug
4.84 out of 5 average rating, 219 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Townhouse in Gloucester
Between 2 Beaches
3 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 197 reviews
Superhost
Home in Gloucester
Stay at Good Harbor Beach
3 bedrooms, 4 beds
10–15 Aug
New place to stay