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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, (258)
"Very private"
The price is ₹11,079
₹14,471 total
includes taxes & fees
13 Nov - 14 Nov
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (205)
"Beautiful accommodations, friendly staff Excellent communication and very clean "
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
9.6 out of 10, Exceptional, (127)
"-"
The price is ₹14,235
₹18,348 total
includes taxes & fees
18 Nov - 19 Nov
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, (1001)
"The property was relatively within a short drive of the places I planned to visit. Loved it. Can't wait to return for the Essex Polar Express event. "
The price is ₹6,542
₹7,523 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn Old Saybrook - Westbrook
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (482)
"Staff was very helpful and welcoming. Views are absolutely amazing and made our one night stay that much more memorable. "
The price is ₹13,227
₹16,899 total
includes taxes & fees
1 Dec - 2 Dec
Sound View Greenport
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 133 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.