Search results; Over 1,000 places in Southold

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Guest favorite
Private room in South End
Vine + Sand Southold, NY's Newest B&B-Room 3
2 guests1 bedroom1 bed1 private bath
Jul 6 – 11
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Jul 6 – 11
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R53,502 ZAR for 5 nights

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Top guest favorite
Home in Southold
North Fork Gem: Wine+Beach+Relax
3 beds
Sep 5 – 10
R44,758 ZAR for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
WaterfrontKayak,
Jul 14 – 19
R79,274 ZAR for 5 nights
5.0 out of 5 average rating, 34 reviews
Guest favorite
Apartment in Southold
Bright, Southold Studio Apt near beach & town
2 beds
Jul 25 – 30
R31,331 ZAR for 5 nights
4.94 out of 5 average rating, 124 reviews
Guest favorite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
3 beds
Jul 13 – 18
R32,997 ZAR for 5 nights
4.9 out of 5 average rating, 177 reviews
Top guest favorite
Room in Mattituck
Stay with NancyHosting for 8 years,
1780 House East Room Country Charm - Downtown
Aug 17 – 22
R16,551 ZAR for 5 nights
4.94 out of 5 average rating, 180 reviews
Home in Southold
Spacious Ranch. Walk to Beach and Southold Village
5 beds
Jul 8 – 13
R63,494 ZAR for 5 nights
New place to stay
Guest favorite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 king bed
Jul 13 – 18
R27,063 ZAR for 5 nights
4.94 out of 5 average rating, 128 reviews
Guest favorite
Home in Southold
Sunset Ranch
3 beds
Jul 12 – 17
R40,595 ZAR for 5 nights
4.91 out of 5 average rating, 11 reviews
Top guest favorite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 king bed
Aug 31 – Sep 5
R19,881 ZAR for 5 nights
4.95 out of 5 average rating, 95 reviews
Guest favorite
Condo in Greenport
Sound Front Condominium
3 beds
Jul 20 – 25
R75,881 ZAR for 5 nights
4.87 out of 5 average rating, 221 reviews
Top guest favorite
Home in Southold
Salt & Sea House - Near wineries, farms, & beaches
3 beds
Jul 7 – 12
R68,491 ZAR for 5 nights
5.0 out of 5 average rating, 40 reviews
Top guest favorite
Home in Southold
Spacious Home with Pool in Southold
7 beds
Aug 3 – 8
R162,274 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Condo in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
3 beds
Aug 31 – Sep 5
R39,970 ZAR for 5 nights
4.92 out of 5 average rating, 142 reviews
Superhost
Home in Southold
Southold Sea'renity
Lake views
Jul 4 – 10
R91,182 ZAR for 6 nights
4.81 out of 5 average rating, 42 reviews
Guest favorite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Kayak
Aug 25 – 30
R68,074 ZAR for 5 nights
4.94 out of 5 average rating, 32 reviews
Top guest favorite
Home in Southold
Private Waterfront home with Dock!
5 beds
Jul 26 – 31
R108,252 ZAR for 5 nights
5.0 out of 5 average rating, 12 reviews
Superhost
Condo in Greenport
Seaside Summer Escape: 2BR Waterfront Condo w/Pool
5 beds
Aug 10 – 15
R57,561 ZAR for 5 nights
4.85 out of 5 average rating, 138 reviews
Guest favorite
Home in Greenport
Beachfront Greenport Villa
Sea views
Jul 16 – 21
R165,064 ZAR for 5 nights
5.0 out of 5 average rating, 63 reviews