A calm lake with a forest in the background during sunset.

Southold Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Southold holiday rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is HK$1,327
HK$2,386 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is HK$2,091
HK$2,389 total
includes taxes & fees
20 Oct - 21 Oct
North Fork Resort
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is HK$746
HK$1,955 total
includes taxes & fees
2 Nov - 3 Nov
Harbor Heights
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

4. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is HK$4,909
HK$8,559 total
includes taxes & fees
15 Oct - 16 Oct
Beachfront Greenport Villa
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

5. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$746
HK$1,937 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

6. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (56 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is HK$746
HK$1,937 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A wooden pathway leading to a beach with scattered rocks and greenery.

7. 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 HK$1,530
HK$3,524 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A beach with people relaxing, a pier extending into the water, and a clear sky.

8. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is HK$1,138
HK$2,941 total
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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 HK$1,562
HK$2,403 total
includes taxes & fees
15 Oct - 16 Oct
American Beech in Greenport - Petite King Room 7
A modern dining area with a wooden table, white chairs, and a chandelier.

10. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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 HK$2,260
HK$4,761 total
includes taxes & fees
20 Oct - 21 Oct
Northfork Townhouse walk to all
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

11. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is HK$2,296
HK$4,847 total
includes taxes & fees
2 Nov - 3 Nov
Renovated Townhouse walk to all
A modern living room with a sofa, coffee table, and dining area.

12. 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 HK$3,995
HK$7,263 total
includes taxes & fees
19 Oct - 20 Oct
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

13. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is HK$4,227
HK$9,107 total
includes taxes & fees
15 Oct - 16 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

14. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is HK$1,766
HK$3,999 total
includes taxes & fees
19 Oct - 20 Oct
Charming Accommodations in the Hamptons
A rocky beach with clear water and a forested hillside in the background.

15. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is HK$4,003
HK$9,836 total
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is HK$4,693
HK$10,136 total
includes taxes & fees
19 Oct - 20 Oct
Amazing Southampton Home with Private Heated Pool
Room

17. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"The room was nice but the bed was horrible. They need to replace the bed ASAP. It is so old that the middle of the bed is touching the floor due to it being worn out. Our backs are still hurting. Otherwise it was a nice room."
United States
William
The price is HK$1,120
HK$1,493 total
includes taxes & fees
15 Oct - 16 Oct
Windward Shores Ocean Resort
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

18. 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 HK$471
HK$3,388 total
includes taxes & fees
18 Oct - 19 Oct
Steps to the beach | Seabreeze Cottage #3
A tented accommodation with a bed, a small table, and a chair.

19. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding place"
United States
Michael H.
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

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

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is HK$2,237
HK$4,609 total
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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

Shorewood Inn

Shorewood Inn

10/10 Excellent
"Clean, affordable, helpful staff, good parking. We will stay again when we are in the area."
Kathleen 1-night trip
Posted 1 hour ago
Shorewood Inn

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 holiday rental in Southold?

Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, 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.

What are some of the best holiday rentals that Southold has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This holiday home rental outside of Southold offers an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Southold?

With 118 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?

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 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.