Southold Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Southold vacation rentals

Individually decorated, individually furnished, iron/ironing board

Aparthotel in Napeague

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (308 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is NT$4,471
NT$5,960 total
includes taxes & fees
Mar 3 - Mar 4
Windward Shores Ocean Resort
Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

Cottage in Greenport

North Fork Cottages & RV Resort
3.0 star property
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is NT$8,119
NT$9,276 total
includes taxes & fees
Apr 1 - Apr 2
North Fork Cottages & RV Resort
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

Hotel Indigo East End by IHG

Hotel Indigo East End by IHG

10/10 Excellent
"Room was spotless, the stuff was excellent. The thing I can really complain about was my dinner coming out last and the food coming out way to hard and late, other than that I love the atmosphere. "
Keith 2-night trip
Posted 2 days ago
Hotel Indigo East End by IHG

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:

  • 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 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 120 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 McCabe's Beach are a couple of lovely local spots to get outside and enjoy nature. While here, The Old Field Vineyards 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.