Find Vacation Rentals in Southold

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Popular Southold Vacation Rentals

Find the perfect Southold vacation rental

Bed and breakfast Southold
from $646 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Room 4)

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Bed and breakfast Southold
from $646 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Room 3)

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Cabin Southold
from $265 per night
6 guests ∙ 3 bedrooms

Cabin

5.0
Outstanding(11 ratings)
Southold, Suffolk County, New York, United States
Vrbo
Details
House Southold
from $353 per night
5 guests ∙ 2 bedrooms

House

5.0
Outstanding(14 ratings)
Southold, Suffolk County, New York, United States
Vrbo
Details
Bed and breakfast Southold
from $808 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Bed and breakfast Southold
from $646 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Room 2)

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Bed and breakfast Southold
from $941 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Bed and breakfast Southold
from $755 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Room 1)

4.8
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
HomeToGo
Details
Bed and breakfast Southold
from $401 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

A Walk in the Woods Bed and Breakfast

Southold, Suffolk County, New York, United States
Vio.com
Details
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Recommended Rentals With Pools

House  Southold
from $843 per night
House ∙ 10 guests ∙ 5 bedrooms

279 m² House

4.9
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
Pool
Vrbo
Details
House  Southold
from $495 per night
6 guests ∙ 3 bedrooms

House

4.9
Outstanding(48 ratings)
Southold, Suffolk County, New York, United States
Pool
Vrbo
Details
House  Southold
from $872 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(57 ratings)
Southold, Suffolk County, New York, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Southold
from $371 per night
House ∙ 4 guests ∙ 2 bedrooms

139 m² House

4.8
Outstanding(13 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Vrbo
Details
House  Southold
from $639 per night
House ∙ 7 guests ∙ 3 bedrooms

163 m² House

5.0
Outstanding(11 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Vrbo
Details
House  Southold
from $645 per night
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

5.0
Outstanding(22 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Vrbo
Details
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Vacation rentals with a balcony

Cottage  Southold
from $534 per night
4 guests ∙ 3 bedrooms

Cottage

4.8
Outstanding(141 ratings)
Southold, Suffolk County, New York, United States
Balcony
Vrbo
Details
House  Southold
from $285 per night
4 guests ∙ 1 bedroom

House

5.0
Outstanding(6 ratings)
Southold, Suffolk County, New York, United States
Balcony
Vrbo
Details
House  Southold
from $402 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(29 ratings)
Southold, Suffolk County, New York, United States
Balcony
Vrbo
Details
Show more

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 $208 per night.

Are there any vacation rentals available to book in Southold?

Tripping.com offers great selection on vacation rentals with 15 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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