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Check prices for these dates

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Top Holiday Rentals in Southold

Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (272)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is ₹11,419
₹14,915 total
includes taxes & fees
25 Mar - 26 Mar
Windward Shores Ocean Resort
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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Other types of properties in Southold you may be interested in

The Shoals Suites and Slips
Garden Suite King | Premium bedding, down duvets, individually decorated

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (149)
"I can’t say enough great things about this place. Absolutely wonderful ! "
The price is ₹14,671
₹16,762 total
includes taxes & fees
9 Mar - 10 Mar
The Shoals Suites and Slips
Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1002)
"I love this property! I stayed for one night and there was a comedian and a lot of activity in the hotel which made for a great night! My only complaint is the bed! It was probably the least comfortable bed I have ever slept in a hotel. I had a horrible night sleep as the mattress was terrible! The room and amenities are all top notch! I am not a fan of the blue toilet water as a cleaner… but just my personal opinion. "
The price is ₹14,742
₹18,448 total
includes taxes & fees
9 Mar - 10 Mar
Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.6 out of 10, Good, (918)
"Perfect place for our short stay, super clean and comfortable!"
The price is ₹5,980
₹6,877 total
includes taxes & fees
2 Mar - 3 Mar
Pier Blue Inn Old Saybrook - Essex
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.

Frequently asked questions

Can I find a holiday rental in Southold?

Yes, there are holiday rentals close to the most popular sights in Southold, 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 129 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 Horton Point Park 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.