Southold Vacation Rentals

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Check prices for these dates

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Aug 14 - Aug 15
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Vacation Rentals in Southold

Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (290)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is ₩265,715
₩333,592 total
includes taxes & fees
Sep 2 - Sep 3
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (235)
"Great location, great views. Walls are a little thin."
The price is ₩457,348
₩582,442 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
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

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"clean, nice staff"
beth 1-night trip
Posted 14 hours ago
Greenview Inn Riverhead

Frequently asked questions

Can I find a vacation rental in Southold?

Yes, we offer vacation rentals in Southold close to Custer Institute and Observatory, or you can select a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals are there in Southold?

With 125 Expedia vacation rentals, you're sure to find just the right place for your Southold stay.

What’s there to see and do in Southold?

McCabe's Beach and Horton Lane Beach 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 vacation rental in Southold like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Southold. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.