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Search results; Over 1,000 places in Southold

Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 king bed
22–27 Apr
4.94 out of 5 average rating, 97 reviews
Guest favourite
Home in Southold
Gorgeous home with heated gunnite pool!
5 beds
28 Apr – 3 May
5.0 out of 5 average rating, 9 reviews
Home in Southold
Summer Retreat at the beach , enjoy Wine Country
4 beds
29 Apr – 5 May
4.81 out of 5 average rating, 67 reviews
Guest favourite
Home in Southold
Horton House
4 beds
20–25 Apr
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 queen bed
27 Apr – 2 May
4.95 out of 5 average rating, 40 reviews
Superhost
Cottage in Southold
Quaint Cottage Close to LI Sound
2 beds
21–26 Apr
4.89 out of 5 average rating, 19 reviews
Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
2 beds
28 Apr – 3 May
4.96 out of 5 average rating, 100 reviews
Guest favourite
Home in Southold
Salt & Sea House - Near wineries, farms, & beaches
3 beds
21–26 Apr
5.0 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Southold
Adorable Cottage
2 queen beds
20–25 Apr
4.95 out of 5 average rating, 21 reviews
Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
4 beds
28 Apr – 3 May
4.94 out of 5 average rating, 32 reviews
Guest favourite
Home in Southold
Le Petit Cottage Southold NY
3 beds
1–6 May
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Southold
Comfortable Cottage on the Great Pond near beach.
3 beds
28 Apr – 3 May
4.9 out of 5 average rating, 151 reviews
Guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 beds
21–26 Apr
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Southold
Southold Comfort - North Fork Getaway
4 beds
19–24 Apr
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Southold
Greenport walk to beach & vineyard! Brand new home
4 beds
26 Apr – 1 May
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Southold
Bright Oasis in Beautiful North Fork Wine Country
5 beds
28 Apr – 3 May
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Greenport
Greenport Beach House
10 beds
24–29 Apr
4.96 out of 5 average rating, 109 reviews
Guest favourite
Home in Southold
Beach/Lake house Fireplace & Hot Tub, By Wineries
On Kenneys Road BeachKayak, Sea views,
11–16 Jun
4.92 out of 5 average rating, 12 reviews