Search Holiday Rentals in Southold

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
3 Nov - 4 Nov
Tomorrow
4 Nov - 5 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Top Holiday Rentals in Southold

Free WiFi, bed sheets
North Fork Cottages & RV Resort
North Fork Cottages & RV Resort
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great stay! Very clean and new. Comfy beds, great location "
United States
Lisa
The price is ฿6,304
฿7,203 total
includes taxes & fees
4 Nov - 5 Nov
North Fork Cottages & RV Resort
Beach nearby
Cliffside Resort Condominiums
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (245)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is ฿7,238
฿9,674 total
includes taxes & fees
4 Nov - 5 Nov
Cliffside Resort Condominiums
Front of property
Canoe Place Waterfront Residences
Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿64,498
฿78,111 total
includes taxes & fees
23 Nov - 24 Nov
Canoe Place Waterfront Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

10/10 Excellent
"Very nice room for the price. Very clean, clean bed sheets, nice pillows and good mattress. Definitely will stay again."
David 1-night trip
Posted 12 hours ago
Budget Host East End Hotel in Riverhead

Find out more about Southold

Search for holiday rentals in Southold on Expedia! You can easily find your home rentals, villas, holiday apartments in Southold using one of the methods below:

  • View our selection of featured holiday rentals in Southold
  • Use the map to find apartments and other holiday homes in the Southold neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southold while they last

Look no further and take a look at our great range of rental properties in Southold!

Frequently asked questions

Can I find a holiday rental in Southold?

Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, or you can select a more secluded option if you're looking for a relaxing stay. Southold is known for its wineries and beaches. Make sure you have time to check out the gardens and football games during your trip.

How many holiday rentals are there in Southold?

With 124 Expedia holiday rentals, you're guaranteed to find just the right place for your Southold stay.

What’s there to see and do in Southold?

McCabe's Beach and Horton Lane Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and Croteaux Vineyards are other places worth a visit.

What’s a holiday rental in Southold like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southold. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.