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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, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is ₹10,735
₹14,099 total
includes taxes & fees
5 Jan - 6 Jan 2025
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"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, (138)
"We had a great stay at the Shoals! The rooms were sparkling clean and the beds were super comfortable. The front desk staff were welcoming and helpful with dining recommendations. We will definitely return. "
The price is ₹14,393
₹16,426 total
includes taxes & fees
5 Jan - 6 Jan 2025
The Shoals Suites and Slips
Residence Inn by Marriott New York Long Island East End
Property amenity

Residence Inn by Marriott New York Long Island East End

3.0 star property
9.2 out of 10, Wonderful, (870)
"Great "
The price is ₹10,045
₹11,464 total
includes taxes & fees
22 Jan - 23 Jan 2025
Residence Inn by Marriott New York Long Island East End
Hyatt Place Long Island East End
Indoor pool, outdoor pool

Hyatt Place Long Island East End

3.0 star property
9.0 out of 10, Wonderful, (1002)
"The hotel was wonderful , location was prefect . Staff was great . I had a great stay "
The price is ₹9,437
₹10,770 total
includes taxes & fees
2 Jan - 3 Jan 2025
Hyatt Place Long Island East End
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 131 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.