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Guest favorite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
7 guests4 bedrooms4 beds2 baths
Jul 27 – Aug 1
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Jul 27 – Aug 1
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R40,022 ZAR for 5 nights
for 5 nights

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Guest favorite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Free cancellation
Sep 1 – 6
R14,982 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 199 reviews
Home in Gloucester
Gloucester Beach House
Free cancellation
Jul 28 – Aug 2
R28,465 ZAR for 5 nights
for 5 nights
4.88 out of 5 average rating, 26 reviews
Top guest favorite
Apartment in Gloucester
Walk to Good Harbor Beach
Free cancellation
Sep 7 – 12
R18,727 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 123 reviews
Apartment in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
Free cancellation
Aug 3 – 8
R33,323 ZAR for 5 nights
for 5 nights
4.77 out of 5 average rating, 239 reviews
Top guest favorite
Condo in Rockport
Rockport Getaway near ocean, music hall & downtown
Free cancellation
Sep 6 – 11
R21,509 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 72 reviews
Top guest favorite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
Free cancellation
Jul 5 – 10
R71,996 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 27 reviews
Apartment in Gloucester
Coastal Escape with Harbor Views
4 beds
Jul 6 – 11
R38,416 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Gloucester
Refreshing Ocean and Sunset View
Free cancellation
Jul 1 – 6
R59,968 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Guest favorite
Townhouse in Gloucester
Luxury Portside Townhome Steps Niles Beach
Free cancellation
Jul 13 – 18
R134,831 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Vacation home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
3 beds
Sep 20 – 25
R54,040 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 52 reviews
Guest favorite
Apartment in Rockport
Artistic studio with garden, walk to town/beaches
Free cancellation
Jul 18 – 23
R21,838 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 34 reviews
Guest favorite
Room in Gloucester
Stay with DawnArtist,
Annisquam Artist Oasis -Serene Private Upstairs
Jul 20 – 25
R13,269 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 238 reviews
Guest favorite
Condo in Gloucester
The BLVD Gloucester Harbor&RiverViews
2 queen beds
Jul 12 – 17
R45,519 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 28 reviews
Guest favorite
Guest suite in Gloucester
The Cressy Rooms at Stage Fort
Free cancellation
Aug 25 – 30
R20,867 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 97 reviews
Top guest favorite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
Free cancellation
Sep 22 – 27
R46,228 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 82 reviews
Superhost
Guest suite in Gloucester
Charlene's Cheery Gloucester Retreat
Free cancellation
Jul 19 – 24
R24,163 ZAR for 5 nights
for 5 nights
4.65 out of 5 average rating, 89 reviews
Superhost
Guest suite in Gloucester
waterview guest suite
Free cancellation
Aug 3 – 8
R19,476 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 57 reviews
Superhost
Townhouse in Gloucester
3BR OceanviewTownhouse|Walk to downtown|Sleeps 8
5 beds
Jul 13 – 18
R51,471 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 4 reviews