230+ Hotel & Resort Deals in Southold |
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Southold Hotels, Resorts, and Rentals

About Southold Vacation Rentals

There are more than 230 places to stay in Southold that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Southold.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Southold, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Southold. Places to stay near Southold are 1092.16 ft² on average, with prices averaging US $712 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Southold with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types 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: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Southold.

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

Stay Near Southold's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Southold's top attractions, neighborhoods, and points of interest.


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 Hotels, Resorts, and Rentals Nearby 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 hotels or resorts in Southold?

You have a lot of choices in or near Southold. If you need a hotel in the Southold area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Southold:

How many vacation rentals have private pools in Southold?

There are 52 accommodation options with private pools in or near Southold. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 230 in the Southold area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Southold.


People Also Ask

There are 4 hotels in Southold and 194 rentals

Recently Booked Hotels, Resorts, or Rentals in Southold