Search Holiday Rentals in Southold

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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, (262)
"Lovely seaside accommodations. Very clean and comfortable. The location is perfect. The room was just a short walk from the beach. Just minutes away from downtown Montauk. Having a full kitchen is great."
The price is ₹10,659
₹13,999 total
includes taxes & fees
3 Dec - 4 Dec
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
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, (130)
"Our room was close to the road and very noisy. Also we found ants in the kitchenette in the middle of the night. "
The price is ₹14,291
₹18,420 total
includes taxes & fees
8 Dec - 9 Dec
The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (1033)
"Kind staffs!"
The price is ₹6,416
₹7,378 total
includes taxes & fees
8 Dec - 9 Dec
Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (892)
"Everything was satisfactory"
The price is ₹5,825
₹6,698 total
includes taxes & fees
24 Nov - 25 Nov
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.
Beautiful view of the beach with palm trees

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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 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.