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Holiday houses Southold


27 cottages, rentals, vacation residences, apartments and campsites in Southold and its surroundings
 
 
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Classic Southold Country Charmer

Southold
 Holiday home, 111 m² 4 people, 2 bedrooms, 1 bathroom
1.2 km
from center
 
Private Waterfront Home: Dock, Kayaks

Southold
 Holiday home 6 people, 2 bathrooms
1.7 km
from center
 
Bright Oasis in North Fork Wine Country

Southold
 Holiday home, 153 m² 4 people, 4 bedrooms, 2 bathrooms
2.2 km
from center
 
Steve's Place: Heated swimming-pool , 3 bedrooms Southold Home, beach

Southold
 Holiday home 6 people, 3 bedrooms, 2 bathrooms
2.4 km
from center
 
Minnehaha Marvel

Southold
 Holiday home, 223 m² 4 people, 1 bedroom, 2 bathrooms
3 km
from center
 
Watersedge Retreat

Southold
 Holiday home, 139 m² 6 people, 3 bedrooms, 2 bathrooms
3.7 km
from center
 
Shelter Island Hidden Estate

East Marion
 Villa 2 people, 1 bedroom, 1 bathroom
4.8 km
from Southold
 
The Cliffside Resort Condominiums

Greenport
 65 apartments, 51 m² 5 to 6 people (total 378 people)
5 km
from Southold
8.7/10
Sandpoint by Rove Travel Modern 5BR Family House with swimming-pool

Shelter Island
 Holiday home, 359 m² 12 people, 1 bedroom
5.2 km
from Southold
 
Modern on 9th

Greenport
 Holiday home, 139 m² 6 people, 3 bedrooms, 3 bathrooms
5.9 km
from Southold
 
The Endless Summer Cottage

Cutchogue
 Holiday home, 117 m² 6 people, 3 bedrooms, 2 bathrooms
6.2 km
from Southold
 
Cozy Greenport Cottage

Greenport
 Holiday home, 158 m² 10 people, 3 bedrooms, 3 bathrooms
6.4 km
from Southold
 
Walk to beach Long Island Wine Country Home!

Cutchogue
 Holiday home, 167 m² 7 people, 3 bedrooms, 2 bathrooms
6.8 km
from Southold
 
Bright Apartment - half Mi to Greenport Harbor!

Greenport
 Apartment, 56 m² 2 people, 1 bedroom, 1 bathroom
7.4 km
from Southold
9.6/10
Quaint DT Greenport Apt - 2 Mi to Shelter Island!

Greenport
 Apartment, 37 m² 2 people, 1 bedroom, 1 bathroom
7.4 km
from Southold
10/10
Lavender Bay Breezes - Private Bay beach Community

East Marion
 Holiday home, 325 m² 8 people, 4 bedrooms, 3 bathrooms
8.9 km
from Southold
 
renovated and Summer House with Water View

Greenport
 Holiday home 10 people, 4 bedrooms, 3 bathrooms
9.1 km
from Southold
 
Lagoon Lodge: North Fork,Charming 3 bedrooms , Waterfront

East Marion
 Holiday home, 405 m² 8 people, 3 bedrooms, 2 bathrooms
9.6 km
from Southold
 
Villa Ebrar - Luxury with swimming-pool

Sag Harbor
 Villa, 279 m² 8 people, 4 bedrooms, 3 bathrooms
9.8 km
from Southold
 
Respite Ranch: private swimming-pool , spa, beach Access

Mattituck
 Holiday home, 186 m² 6 people, 3 bedrooms, 3 bathrooms
10.4 km
from Southold
 
Entertainment Galore, Meadowood Manor by RoveTravel

Sag Harbor
 Holiday home, 316 m² 12 people, 1 bedroom
10.4 km
from Southold
 
The Briar Patch

East Marion
 Holiday home, 102 m² 6 people, 3 bedrooms, 2 bathrooms
10.4 km
from Southold
 
North Fork Waterfront Gem

East Marion
 Holiday home, 139 m² 4 people, 2 bedrooms, 2 bathrooms
10.6 km
from Southold
 
Mattituck House with fireplaces - close to Wineries

Mattituck
 Holiday home, 135 m² 6 people, 3 bedrooms, 2 bathrooms
10.6 km
from Southold
 
Villa Zainip - Luxury with swimming-pool

Sag Harbor
 Villa, 279 m² 8 people, 5 bedrooms, 4 bathrooms
11.1 km
from Southold
 
Getaway House at Sag Harbor

Sag Harbor
 Holiday home 6 people, 3 bedrooms, 2 bathrooms
11.9 km
from Southold
 
Nature's Paradise: Private Dock & Water Views

Mattituck
 Holiday home, 223 m² 9 people, 4 bedrooms, 4 bathrooms
11.9 km
from Southold
 
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