Find Vacation Rentals in Southold

Southold
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Popular Southold Vacation Rentals

Find the perfect Southold vacation rental

Bed & Breakfast Southold
e.g. 5/31 - 6/7 (Tue - Tue)
-31%
$601
$416 per night
Bed & Breakfast ∙ 14 guests ∙ 1 bedroom
4.6
"Outstanding" (230 ratings)
Southold, Suffolk County, New York, United States
Details
Expedia
Details
Motel Southold
e.g. 8/27 - 9/3 (Sat - Sat)
$264 per night
Motel ∙ 4 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 5/31 - 6/7 (Tue - Tue)
$472 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 9/2 - 9/9 (Fri - Fri)
$573 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 5/31 - 6/7 (Tue - Tue)
$416 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Motel Southold
e.g. 8/27 - 9/3 (Sat - Sat)
$238 per night
Motel ∙ 4 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 5/31 - 6/7 (Tue - Tue)
$416 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 5/28 - 6/4 (Sat - Sat)
$607 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Bed & Breakfast Southold
e.g. 11/19 - 11/26 (Sat - Sat)
$449 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
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Recommended Rentals With Pools

Condo Pool Southold
$376 per night
Condo ∙ 14 guests ∙ 2 bedrooms
4.3
"Very good" (454 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
Expedia
Details
Bed & Breakfast Pool Southold
$449 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
4.4
"Very good" (14 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
trivago’s partner
Details
Apartment Pool Southold
$557 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (23 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
trivago’s partner
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Best vacation rentals with a balcony

Apartment Balcony Southold
$362 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.4
"Very good" (72 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
trivago’s partner
Details
Bed & Breakfast Balcony Southold
$487 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
4.5
"Outstanding" (48 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
trivago’s partner
Details
Apartment Balcony Southold
$331 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.3
"Very good" (15 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
trivago’s partner
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Vacation homes and cottages with a garden

Bed & Breakfast Yard Southold
$271 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Yard
Details
HomeToGo
Details
Bed & Breakfast Yard Southold
$365 per night
Bed & Breakfast ∙ 14 guests ∙ 1 bedroom
5.0
"Excellent" (437 ratings)
Southold, Suffolk County, New York, United States
Yard
Details
Expedia
Details
Bed & Breakfast Yard Southold
$307 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Southold, Suffolk County, New York, United States
Yard
Details
HomeToGo
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Southold on average?

Prices for a stay in Southold begin at $253 per night.

Are there any vacation rentals available to book in Southold?

Tripping.com offers great selection on vacation rentals with 33 offers currently available in Southold.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Southold

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Southold offers 270 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Southold start at an average price of $413 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 243 of Southold’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 50 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 236 vacation home rentals. Traveling with your dog or cat? Choose from 71 pet-friendly rentals in Southold that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 6 vacation rental sites in Southold where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 216 HomeAway rentals, 26 TripAdvisor short term rentals and 16 Booking.com vacation rentals.

Popular Day Trips Near Southold

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