Southold Vacation Rentals

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Vacation Rentals in Southold

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Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is RM 851
per night
23 May - 24 May
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 RM 873
per night
29 May - 30 May
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 duvets, individually decorated
The Shoals Suites and Slips
3.5 star property
9.6 out of 10, Exceptional, (77)
"great room, great size, clean, nice.....just not a fan of the weighted blankets on the beds! "
The price is RM 1,386
per night
23 May - 24 May
The Shoals Suites and Slips
Breakfast and dinner served
Hilton Garden Inn Riverhead
3.0 star property
8.6 out of 10, Excellent, (1000)
"Very comfortable and warm feeling "
The price is RM 633
per night
2 Jun - 3 Jun
Hilton Garden Inn Riverhead
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (780)
"This is a no-frills hotel. However we had a mini fridge, microwave and coffee maker in our room. VERY spacious. Staff were friendly and at the front desk when we needed them to be there. A lady came to our door once to see if we needed fresh towels (we were there for 6 days). We will stay here on a return visit. Thanks Pier Blue staff"
The price is RM 417
per night
29 May - 30 May
Pier Blue Inn Old Saybrook - Essex
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.co.uk! 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 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 128 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.

Recent reviews of Southold properties
Expedia verified reviews

The Niantic Inn

The Niantic Inn

5/5 Excellent
"Very nice accommodations. "
A verified traveller stayed at The Niantic Inn
Posted 3 days ago
The Niantic Inn