Southold Vacation Rentals

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Vacation Rentals in Southold

View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (235)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is P8,846
P11,346 total
includes taxes & fees
May 19 - May 20
Windward Shores Ocean Resort
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is P14,156
P18,656 total
includes taxes & fees
May 19 - May 20
Cliffside Resort Condominiums
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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.

Other types of properties in Southold you may be interested in

Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips
3.5 star property
9.6 out of 10, Exceptional, (75)
"Would go back in a heartbeat. The staff were so friendly and the rooms are gorgeous. Honestly it’s a best kept secret and I’m so glad we found it! "
The price is P16,976
P20,812 total
includes taxes & fees
May 20 - May 21
The Shoals Suites and Slips
Breakfast and dinner served
Hilton Garden Inn Riverhead
3.0 star property
8.6 out of 10, Excellent, (1001)
"comfortable and courteous. Enjoyed the goodie bag we received when checking in."
The price is P7,403
P8,449 total
includes taxes & fees
May 22 - May 23
Hilton Garden Inn Riverhead
Property amenity
Residence Inn by Marriott New York Long Island East End
3.0 star property
9.2 out of 10, Wonderful, (769)
"Room size was perfect"
The price is P8,277
P9,446 total
includes taxes & fees
May 21 - May 22
Residence Inn by Marriott New York 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.

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:

  • View our selection of featured holiday rentals in Southold
  • Use the map to find apartments and other holiday homes in the Southold neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southold while they last

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 close to top sights in Southold, or you can choose a secluded option if you'd like a relaxing place to 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 vacation rentals are there in Southold?

With 129 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?

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 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.

Recent reviews of Southold properties
Expedia verified reviews

Sag Harbor Inn

Sag Harbor Inn

5/5 Excellent
"Kind and clean "
A verified traveler stayed at Sag Harbor Inn
Posted 2 days ago
Sag Harbor Inn