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Search results; Over 1,000 places in Southold

Superhost
Cottage in Southold
Quaint Cottage Close to LI Sound
2 beds
Apr 21 – 26
4.89 out of 5 average rating, 19 reviews
Guest favorite
Home in Southold
Gorgeous home with heated gunnite pool!
5 beds
Apr 28 – May 3
5.0 out of 5 average rating, 9 reviews
Guest favorite
Guesthouse in Southold
Southold- Adorable 1 Bedroom Cottage
1 queen bed
Apr 27 – May 2
4.95 out of 5 average rating, 40 reviews
Guest favorite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 king bed
Apr 22 – 27
4.94 out of 5 average rating, 97 reviews
Guest favorite
Apartment in Southold
Bright, Southold Studio Apt near beach & town
2 beds
Apr 28 – May 3
4.96 out of 5 average rating, 100 reviews
Guest favorite
Home in Southold
Le Petit Cottage Southold NY
3 beds
May 1 – 6
5.0 out of 5 average rating, 14 reviews
Guest favorite
Home in Southold
Salt & Sea House - Near wineries, farms, & beaches
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 31 reviews
Cottage in Southold
Cozy&Chic Beach Cottage (Great 4 remote work too)
3 beds
Apr 21 – 26
4.78 out of 5 average rating, 160 reviews
Guest favorite
Home in Southold
Farm house with vineyard views
4 beds
Apr 21 – 26
4.93 out of 5 average rating, 14 reviews
Guest favorite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 beds
Apr 22 – 27
5.0 out of 5 average rating, 9 reviews
Guest favorite
Cottage in Southold
Adorable Cottage
2 queen beds
Apr 20 – 25
4.95 out of 5 average rating, 21 reviews
Guest favorite
Cottage in Southold
Comfortable Cottage on the Great Pond near beach.
3 beds
Apr 28 – May 3
4.9 out of 5 average rating, 151 reviews
Guest favorite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
4 beds
Apr 28 – May 3
4.94 out of 5 average rating, 32 reviews
Guest favorite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 king bed
Apr 21 – 26
4.96 out of 5 average rating, 74 reviews
Guest favorite
Home in Southold
Greenport walk to beach & vineyard! Brand new home
4 beds
Apr 26 – May 1
5.0 out of 5 average rating, 25 reviews
Guest favorite
Home in Southold
Beach/Lake house Fireplace & Hot Tub, By Wineries
On Kenneys Road BeachKayak, Sea views,
Jun 11 – 16
4.92 out of 5 average rating, 12 reviews
Guest favorite
Home in Southold
Bright Oasis in Beautiful North Fork Wine Country
5 beds
Apr 28 – May 3
4.96 out of 5 average rating, 26 reviews
Guest favorite
Home in Southold
Southold Comfort - North Fork Getaway
4 beds
Apr 19 – 24
5.0 out of 5 average rating, 32 reviews