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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Southold vacation rentals

Condo | Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
The price is AED 1,126
AED 1,614 total
includes taxes & fees
9 Sep - 10 Sep
Cliffside Resort Condominiums
Flat-screen TV

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (45 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AED 1,167
AED 1,333 total
includes taxes & fees
7 Sep - 8 Sep
North Fork Resort
Sun loungers, beach towels

3. Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (40 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is AED 716
AED 1,381 total
includes taxes & fees
8 Sep - 9 Sep
Aqua Vista
Sun loungers, beach towels

4. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 900
AED 1,897 total
includes taxes & fees
7 Sep - 8 Sep
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Terrace/patio

5. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AED 1,135
AED 1,649 total
includes taxes & fees
7 Sep - 8 Sep
American Beech in Greenport - Petite King Room 7
1 bedroom, desk, iron/ironing board, travel crib

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 453
AED 866 total
includes taxes & fees
10 Sep - 11 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
1 bedroom, bed sheets

7. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is AED 789
AED 1,196 total
includes taxes & fees
16 Aug - 17 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Sun loungers, beach towels

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is AED 1,818
AED 2,854 total
includes taxes & fees
26 Aug - 27 Aug
The SandPiper
Beach

9. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (21 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is AED 1,084
AED 1,884 total
includes taxes & fees
3 Sep - 4 Sep
Harbor Heights
Beach

10. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything was so nice and clean. Location was great, walking distance from everything. My children had an amazing time. I would book this again in the summer."
United States
Jessica0610@gmail.com A.
The price is AED 1,084
AED 2,014 total
includes taxes & fees
8 Sep - 9 Sep
Beach Block Hideaway
1 bedroom, bed sheets

11. Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is AED 710
AED 1,089 total
includes taxes & fees
13 Aug - 14 Aug
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
Beach nearby

12. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AED 793
AED 2,291 total
includes taxes & fees
17 Aug - 18 Aug
Seabreeze 4 Charming Cottage footsteps to beach
1 bedroom, bed sheets

13. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is AED 710
AED 1,089 total
includes taxes & fees
13 Aug - 14 Aug
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Beach nearby

14. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AED 573
AED 1,094 total
includes taxes & fees
12 Aug - 13 Aug
The Stern at Soundview · Beach+Ocean+Sunrise
Dining

15. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (5 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is AED 579
AED 1,236 total
includes taxes & fees
16 Aug - 17 Aug
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Sun loungers, beach towels

16. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is AED 579
AED 1,344 total
includes taxes & fees
24 Aug - 25 Aug
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Coffee/tea maker, fridge, microwave, oven

17. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (26 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 735
AED 1,309 total
includes taxes & fees
1 Sep - 2 Sep
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

18. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
The price is AED 1,134
AED 2,273 total
includes taxes & fees
23 Aug - 24 Aug
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Interior

19. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AED 718
AED 1,643 total
includes taxes & fees
12 Aug - 13 Aug
Adorable Cottage, 5 min walk to water & town
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

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"a"
Heather 1-night trip
Posted 5 hours ago
The Pridwin Hotel

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 118 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 Mattebella 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.