Southold Vacation Rentals - HolidayHomes base64Hash Southold Vacation Rentals - HolidayHomes

Southold Vacation Rentals

Browse 191 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Southold

Book the highest-rated Southold vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Southold
House with yard | Nature view
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House Southold
Vacation home with patio, garden & grill
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House Southold
Vacation home with terrace, barbeque & private pool
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House Southold
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
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House Southold
North Beach Fork Beach House
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Cabin Southold
Cottage with BBQ, garden & terrace | Nature view
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House Southold
6BR, Saltwater Pool, Bocce, Hot Tub, Sauna. Walk to beach, minutes to vineyards!
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House Southold
Family-friendly nice vacation home with garden, terrace & private pool | Suitable for remote work | Pets allowed
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House Southold
Shorecrest Beach House Beach Front Ocean views
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House Southold
Southold Soundfront Private Beach
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House Southold
Waterfront, New Construction North Fork Beach House
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House Southold
House of Classic Arts and Crafts North Fork
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House Southold
Between the Vineyard and Sea. Walk to sandy beach from this charming cottage.
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House Southold
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
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House Southold
Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach
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Top 15 most Recommended Vacation Rentals in Southold

Discover your ideal Southold vacation rental with real-time comparisons of 191 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Southold
8 guests ∙ 4 bedrooms

House

Southold, Suffolk County, New York, United States
This North Fork house rental accommodates 8 guests and features a private pool for a relaxing getaway.
from $489
per night
(2)
View deal
House Southold
House ∙ 10 guests ∙ 5 bedrooms

297 m² House

Southold, Suffolk County, New York, United States
This spacious house rental in North Fork accommodates 10 guests and features a private pool for relaxation and enjoyment.
from $689
per night
(89)
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

102 m² House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 6 guests and features a cozy fireplace for a comfortable stay.
from $483
per night
(8)
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House Southold
7 guests ∙ 3 bedrooms

House

Southold, Suffolk County, New York, United States
Charming house rental in North Fork with a capacity for 7 featuring a cozy fireplace and lovely lakeview.
from $677
per night
(12)
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House Southold
2 guests ∙ 1 bedroom

House

Southold, Suffolk County, New York, United States
Cozy house rental in North Fork comfortably accommodates 2 guests and features a charming outdoor patio for relaxation.
from $241
per night
(2)
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House Southold
6 guests ∙ 3 bedrooms

House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 6 guests and features a private pool for a relaxing getaway.
from $721
per night
(20)
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House Southold
House ∙ 4 guests ∙ 3 bedrooms

112 m² House

Southold, Suffolk County, New York, United States
Charming house rental in North Fork accommodating 4 guests with a spacious yard perfect for outdoor relaxation.
from $419
per night
(7)
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House Southold
6 guests ∙ 3 bedrooms

House

Southold, Suffolk County, New York, United States
This North Fork house rental accommodates 6 guests and features a spacious yard perfect for family gatherings.
from $518
per night
(80)
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

297 m² House

Southold, Suffolk County, New York, United States
Spacious house rental in North Fork accommodates 10 guests and features a cozy fireplace for a warm, inviting atmosphere.
from $571
per night
(29)
View deal

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