Southold Vacation Rentals

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Vacation Rentals in Southold

Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is P7,401
P9,720 total
includes taxes & fees
Dec 2 - Dec 3
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
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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Other types of properties in Southold you may be interested in

The Shoals Suites and Slips
Premium bedding, down comforters, individually decorated

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (130)
"The Shoals is really such a cute place. The rooms are spacious and very clean. My sisters and I stayed here for the second time in November. Last time I stayed during the week and it was very quiet. However this time we had someone staying next to us and you can hear the TV like it’s in your room as it is up against your bed wall and just someone walking was loud. Thankfully they didn’t keep the TV on all night. When you arrive at the Shoals there is someone at the front desk but they leave by...
The price is P9,923
P12,790 total
includes taxes & fees
Dec 15 - Dec 16
The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.4 out of 10, Good, (1085)
"My mattress was less than good and needs to be replaced. Otherwise, the facility was clean and reasonable with a good breakfast."
The price is P4,879
P5,611 total
includes taxes & fees
Dec 15 - Dec 16
Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.6 out of 10, Good, (892)
"It’s centrally located. The staff was friendly and accommodating. The room was clean and the water pressure was fantastic. I would recommend. "
The price is P4,044
P4,651 total
includes taxes & fees
Dec 2 - Dec 3
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.

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 130 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, Sannino's Bella Vita Vineyard and Sparkling Pointe 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.