229+ Luxury Vacation Rentals & Cabins in Southold |
  1. USA
  2. New York
  3. Southold

Southold Cabin Rentals

About Southold Vacation Rentals

There are more than 229 incredible getaway rentals that are available in Southold. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Southold.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Southold, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Southold. Places to stay near Southold are 1091.7 ft² on average, with prices averaging US $709 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Southold. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

Show more
Show less

Top Cabin Rentals, Cottages, and Holiday Home Rentals in Southold

Type Count
Vacation Homes 189
Cottages 20
Others 7
Holiday Apartments 5
B&B 5

Use these Quick Filters to Find a Vacation Rental in Southold

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Southold with Cabinns.com.

Weather in Southold, NY

View the weather forecast for Southold before booking your Southold Vacation Rentals to confirm your best time to go.

December - February
High 42°F       Low 22°F
March - May
High 65°F       Low 23°F
June - August
High 79°F       Low 58°F
September - November
High 75°F       Low 32°F

Activities Southold Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Southold. Discover Top Attractions For Your Next Outdoor Adventure.


Sparkling Pointe
The Old Field Vineyards
Mattebella Vineyards
Horton Point Park
Sannino's Bella Vita Vineyard
Croteaux Vineyards
Osprey's Dominion
Horton Lane Beach
Cooper's Beach
Splish Splash Water Park
Essex Steam Train
East Hampton Main Beach
Wolffer Estates Vineyard
Hammonasset Beach State Park
Tanger Outlet Center
Meschutt Beach
Guild Hall
Essex Library
Hither Hills State Park
Clinton Crossing Premium Outlets

Find Nearby Cabin Rentals in these Cities & Neighborhoods


The Old Field Vineyards 375 Properties
Croteaux Vineyards 296 Properties
Mattebella Vineyards 295 Properties
Osprey's Dominion 291 Properties
Sannino's Bella Vita Vineyard 279 Properties
Sparkling Pointe 260 Properties
Horton Lane Beach 202 Properties
Horton Point Park 183 Properties

Frequently Asked Questions About Southold?

What are the top cabins, lake houses & summer homes in Southold?

We provide an array of great vacation destinations in Southold. If you are looking to stay in or around the Southold area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Southold:

How many cabin rentals and resorts have private pools in Southold?

We have 42 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Southold. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Southold is best for families?

Searching for a family-friendly cabin in Southold? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Southold?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 229 in the Southold area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Southold.


People Also Ask

There are 3 hotels in Southold and 194 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Southold