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Search results; Over 1,000 places in Southold

Guest favourite
Room in Southold
Stay with RobertRetired,
Cozy guest room - quiet getaway - wine country
11–16 Apr
4.99 out of 5 average rating, 115 reviews
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 king bed
2–7 Apr
4.94 out of 5 average rating, 95 reviews
Superhost
Cottage in Southold
Quaint Cottage Close to LI Sound
2 beds
2–7 Apr
4.89 out of 5 average rating, 18 reviews
Guest favourite
Guest suite in Cutchogue
Walk to Vineyards, Beaches, Farms & Town
1 king bed
7–12 Apr
4.88 out of 5 average rating, 582 reviews
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 queen bed
1–6 Apr
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Southold
Gorgeous home with heated gunnite pool!
5 beds
7–12 Apr
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Southold
Le Petit Cottage Southold NY
3 beds
1–6 Apr
5.0 out of 5 average rating, 14 reviews
Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
2 beds
1–6 Apr
4.96 out of 5 average rating, 100 reviews
Guest favourite
Home in Southold
Horton House
4 beds
6–11 Apr
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Southold
Beach/Lake house ~ Fireplace ~ North Fork Wineries
6 beds
1–6 Apr
4.92 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Southold
Adorable Cottage
2 queen beds
1–6 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
8–13 Apr
4.94 out of 5 average rating, 32 reviews
Guest favourite
Home in Southold
Bright Oasis in Beautiful North Fork Wine Country
5 beds
14–19 Apr
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 beds
8–13 Apr
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Southold
Salt & Sea House - Near wineries, farms, & beaches
3 beds
1–6 Apr
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Southold
Greenport walk to beach & vineyard! Brand new home
4 beds
1–6 Apr
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
5 beds
1–6 Apr
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Southold
NEW LISTING: COMPLETELY RENOVATED 4-BED, 3-BATH
4 beds
1–6 Apr
4.94 out of 5 average rating, 18 reviews