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$1,326
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$2,140
HK$2,445 total
includes taxes & fees
1 Nov - 2 Nov
North Fork Resort
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

3. 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 beach with people relaxing on chairs and sunbathing.

4. 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$1,928 total
includes taxes & fees
9 Nov - 10 Nov
Harbor Heights
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 relaxing, a pier extending into the water, and a clear sky.

6. 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
10 Nov - 11 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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$3,533 total
includes taxes & fees
10 Nov - 11 Nov
Beach Block Hideaway
An outdoor dining area with hanging lights, palm trees, and a bar.

8. 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$2,385 total
includes taxes & fees
20 Oct - 21 Oct
American Beech in Greenport - Petite King Room 7
Room

9. 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
18 Oct - 19 Oct
Windward Shores Ocean Resort
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

10. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$596
HK$3,535 total
includes taxes & fees
27 Oct - 28 Oct
Walk to Beach | Seabreeze Cottage #4
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

11. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (62 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$812
HK$1,624 total
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A modern dining area with a wooden table, white chairs, and a chandelier.

12. 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$2,048
HK$4,519 total
includes taxes & fees
2 Nov - 3 Nov
Northfork Townhouse walk to all
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

13. 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
20 Oct - 21 Oct
Charming Accommodations in the Hamptons
A dining area with a round table, six chairs, and a chandelier.

14. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$487
HK$9,869 total
includes taxes & fees
21 Oct - 22 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A modern building with large windows overlooking a beach.

15. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is HK$691
HK$9,151 total
includes taxes & fees
18 Oct - 19 Oct
Beachfront Jacuzzi All Year - Black Swan Home
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.

16. 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$2,260
HK$4,797 total
includes taxes & fees
10 Nov - 11 Nov
Renovated Townhouse walk to all
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

17. 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
21 Oct - 22 Oct
Steps to the beach | Seabreeze Cottage #3
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

18. 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, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is HK$1,130
HK$2,502 total
includes taxes & fees
20 Oct - 21 Oct
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

19. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$1,491
HK$4,923 total
includes taxes & fees
27 Oct - 28 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A stone pier leading to a beach with houses in the background.

20. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (63 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is HK$883
HK$2,136 total
includes taxes & fees
19 Oct - 20 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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

Zey Hotel

Zey Hotel

10/10 Excellent
"The staff particularly James were over the top accommodating!!"
William 2-night trip
Posted 7 hours ago
Zey Hotel

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.