A calm lake with a forest in the background during sunset.

Southold Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Southold vacation rentals

Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (267 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is ￥72,879
￥90,320 total
includes taxes & fees
Jul 14 - Jul 15
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
The price is ￥60,443
￥69,056 total
includes taxes & fees
Jul 27 - Jul 28
North Fork Resort
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is ￥197,881
￥230,493 total
includes taxes & fees
Jul 28 - Jul 29
Windward Shores Ocean Resort
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
The price is ￥183,142
￥277,316 total
includes taxes & fees
Aug 5 - Aug 6
Hamptons Vacation Rental w/ Saltwater Pool
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Our room was lovely however it was on the second floor of the building with no elevator. There were 14 steep steps that had to be climbed. My husband (84) had trouble doing this. We were not notified of the steps when we made our reservations. When I asked for a different room, I was told they were all filled. Restaurant: Food good but expensive and took a long time to arrive. More stairs to get to the dining room. To use the elevator one needed to pass through the kitchen. Beach: Wall to wall deck chairs. One would have more room at a public beach."
Marjorie 2-night trip
Posted 22 hours ago
Water's Edge Resort & Spa

Find out more about Southold

Search for holiday rentals in Southold on Expedia! You can easily find your home rentals, villas, holiday apartments in Southold using one of the methods below:

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Look no further and take a look at our great range of rental properties in Southold!

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.

What are some of the best vacation home rentals that Southold has to offer?

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!: Visitors give good reviews to this Southold vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Southold?

With 113 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.