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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Southold vacation rentals

A serene lakeside setting with a gazebo and a bird feeder.

1. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Beautiful property, comfortable and very clean!"
United States
Doran R.
The price is AED 918
AED 1,737 total
includes taxes & fees
23 Nov - 24 Nov
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is AED 706
AED 1,214 total
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is AED 1,145
AED 1,308 total
includes taxes & fees
23 Nov - 24 Nov
North Fork Resort
A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is AED 314
AED 837 total
includes taxes & fees
22 Nov - 23 Nov
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is AED 349
AED 852 total
includes taxes & fees
30 Nov - 1 Dec
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is AED 349
AED 881 total
includes taxes & fees
18 Nov - 19 Nov
Aqua Vista
A bathroom with a white sink, a toilet, and a window with blinds.

7. 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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 479
AED 1,278 total
includes taxes & fees
16 Nov - 17 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AED 716
AED 1,574 total
includes taxes & fees
16 Nov - 17 Nov
Beach Block Hideaway
An outdoor dining area with hanging lights, palm trees, and a bar.

9. 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)
"Great place! So nice."
United States
Paul F.
The price is AED 731
AED 1,058 total
includes taxes & fees
16 Nov - 17 Nov
American Beech in Greenport - Petite King Room 7
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

10. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is AED 220
AED 1,668 total
includes taxes & fees
22 Nov - 23 Nov
Steps to the beach | Seabreeze Cottage #3
A modern dining area with a wooden table, white chairs, and a chandelier.

11. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (9 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is AED 1,058
AED 2,128 total
includes taxes & fees
1 Dec - 2 Dec
Northfork Townhouse walk to all
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

12. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
Cozy Cottage by the beach - Seabreeze #1
A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

13. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is AED 843
AED 1,966 total
includes taxes & fees
16 Nov - 17 Nov
Renovated Townhouse walk to all
A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

14. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is AED 2,066
AED 3,703 total
includes taxes & fees
16 Nov - 17 Nov
Beachfront Greenport Villa
A patio with a wooden table and chairs, a door with a number, and a mailbox.

15. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is AED 826
AED 1,821 total
includes taxes & fees
16 Nov - 17 Nov
Charming Accommodations in the Hamptons
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

16. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
The price is AED 554
AED 930 total
includes taxes & fees
19 Nov - 20 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A modern building with large windows overlooking a beach.

17. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
The price is AED 331
AED 4,565 total
includes taxes & fees
16 Nov - 17 Nov
Beachfront Jacuzzi All Year - Black Swan Home
Terrace/patio

18. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (334 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is AED 484
AED 653 total
includes taxes & fees
16 Nov - 17 Nov
Windward Shores Ocean Resort
A deck with outdoor furniture, a grill, and a potted plant.

19. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is AED 1,737
AED 3,068 total
includes taxes & fees
1 Dec - 2 Dec
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A house with a swimming pool, surrounded by trees and a fenced yard.

20. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AED 349
AED 4,346 total
includes taxes & fees
22 Nov - 23 Nov
Jacuzzi year-round - Villa Luz Private Home
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Entire hotel was so clean. Room had everything we needed. Would definitely stay there again"
Tammi 1-night trip
Posted 8 hours ago
Hilton Garden Inn Riverhead

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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: You might want to consider this vacation rental near Southold, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 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 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.