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Southold Holiday Rentals

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Check prices for these dates

Tonight
21 Nov - 22 Nov
Tomorrow
22 Nov - 23 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Southold

Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is S$262
includes taxes & fees
23 Nov - 24 Nov
North Fork Cottages & RV Resort
Front of property
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is S$2,682
includes taxes & fees
21 Dec - 22 Dec
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.
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Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Everything and everyone was fabulous! "
James 1-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

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 123 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?

Horton Lane Beach and McCabe's Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and The Old Field 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.