Search results; Over 1,000 homes in Gloucester

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Top guest favorite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed
Aug 17 – 22
R12,351 ZAR for 5 nights
4.91 out of 5 average rating, 205 reviews
Guest favorite
Room in Gloucester
Stay with KatherineHosting for 8 years,
Award Winning View from Portagee Hill
Jul 17 – 22
R13,464 ZAR for 5 nights
4.87 out of 5 average rating, 212 reviews
Top guest favorite
Apartment in Gloucester
Boulevard Retreat
4 beds
Aug 24 – 29
R28,412 ZAR for 5 nights
5.0 out of 5 average rating, 87 reviews
Guest favorite
Apartment in Magnolia
Bright One Bedroom Apartment 5 Min Walk From Beach
2 beds
Aug 4 – 9
R28,073 ZAR for 5 nights
4.87 out of 5 average rating, 146 reviews
Top guest favorite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
4 beds
Sep 22 – 27
R45,798 ZAR for 5 nights
4.98 out of 5 average rating, 84 reviews
Superhost
Tiny home in Gloucester
Smith Cove Cottgage
2 beds
Jul 27 – Aug 1
R23,111 ZAR for 5 nights
New place to stay
Guest favorite
Home in Annisquam
Annisquam Getaway - Water View+Walk To The Beach
5 beds
Sep 3 – 8
R49,657 ZAR for 5 nights
4.97 out of 5 average rating, 33 reviews
Guest favorite
Apartment in Gloucester
East Gloucester Beach house
4 beds
Aug 31 – Sep 5
R35,515 ZAR for 5 nights
4.9 out of 5 average rating, 40 reviews
Guest favorite
Townhouse in Gloucester
3BR OceanviewTownhouse|Walk to downtown|Sleeps 8
5 beds
Aug 15 – 20
R55,446 ZAR for 5 nights
4.88 out of 5 average rating, 8 reviews
Superhost
Home in Gloucester
Cranberry Hill | 9 BR 22 Acre Estate | Sleeps 24
13 beds
Jul 17 – 22
R194,217 ZAR for 5 nights
New place to stay
Apartment in Gloucester
Seafood, Sunsets + Seaside Charm
2 beds
Aug 23 – 28
R32,335 ZAR for 5 nights
4.9 out of 5 average rating, 31 reviews
Guest favorite
Apartment in Gloucester
E. Gloucester Beach house 2nd FL
3 beds
Sep 8 – 13
R25,020 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Room in Gloucester
Stay with DawnArtist,
Annisquam Artist Oasis -Serene Private Upstairs
Aug 23 – 28
R13,464 ZAR for 5 nights
4.92 out of 5 average rating, 239 reviews
Guest favorite
Condo in Gloucester
KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
2 queen beds
Aug 3 – 8
R46,986 ZAR for 5 nights
4.95 out of 5 average rating, 162 reviews
Apartment in Gloucester
Cozy
Jul 26 – 31
R22,899 ZAR for 5 nights
4.76 out of 5 average rating, 42 reviews
Top guest favorite
Condo in Gloucester
Boho Beach Condo for Ocean Escape
3 beds
Sep 21 – 26
R28,879 ZAR for 5 nights
4.98 out of 5 average rating, 89 reviews
Superhost
Home in Gloucester
Lobster Trap: Beauport, Pavilion Beach, Downtown
4 beds
Jul 20 – 25
R44,441 ZAR for 5 nights
New place to stay
Top guest favorite
Condo in Gloucester
3BR Oceanfront Condo with decks
5 beds
Sep 7 – 12
R35,939 ZAR for 5 nights
4.99 out of 5 average rating, 115 reviews