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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (292 reviews)
"Great place!"
United States
Christine
The price is ￥43,027
￥66,497 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Flat-screen TV

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥43,103
￥49,246 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort
Sun loungers, beach towels

3. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,613
￥47,754 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
Beach

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is ￥22,613
￥49,712 total
includes taxes & fees
Oct 5 - Oct 6
Harbor Heights
Beach

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥38,208
￥71,984 total
includes taxes & fees
Oct 4 - Oct 5
Beach Block Hideaway
Sun loungers, beach towels

6. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥22,613
￥49,890 total
includes taxes & fees
Oct 18 - Oct 19
The SandPiper
Sun loungers, beach towels

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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥27,369
￥66,371 total
includes taxes & fees
Sep 28 - Sep 29
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Terrace/patio

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 ￥35,713
￥51,316 total
includes taxes & fees
Sep 30 - Oct 1
American Beech in Greenport - Petite King Room 7
Smart TV, offices

9. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
8.0 out of 10, Very good, (2 reviews)
"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...
United States
Anonymous traveler
The price is ￥13,256
￥71,793 total
includes taxes & fees
Sep 20 - Sep 21
Seabreeze #3 Cozy Cottage steps to the beach
1 bedroom, desk, iron/ironing board, travel crib

10. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (59 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥18,948
￥36,271 total
includes taxes & fees
Oct 14 - Oct 15
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds

11. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is ￥30,165
￥48,363 total
includes taxes & fees
Sep 20 - Sep 21
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
1 bedroom, bed sheets

12. 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 ￥30,165
￥46,403 total
includes taxes & fees
Sep 20 - Sep 21
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Iron/ironing board, WiFi (free), individually decorated

13. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is ￥18,550
￥25,433 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
Exterior

14. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥38,208
￥85,526 total
includes taxes & fees
Sep 20 - Sep 21
Lovely studio with AC in charming Sag Harbor
Interior

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥25,825
￥73,544 total
includes taxes & fees
Sep 20 - Sep 21
Adorable Cottage, 5 min walk to water & town
Property grounds

16. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
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 ￥17,466
￥261,771 total
includes taxes & fees
Sep 21 - Sep 22
Villa Luz Family Home w/ heated pool & jacuzzi
Sun loungers, beach towels

17. 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥23,159
￥52,950 total
includes taxes & fees
Sep 28 - Sep 29
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Property grounds

18. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥113,688
￥191,180 total
includes taxes & fees
Oct 6 - Oct 7
Beachfront Greenport Villa
Beach nearby

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 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 ￥17,544
￥42,454 total
includes taxes & fees
Sep 29 - Sep 30
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Dining

20. 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 ￥23,860
￥51,494 total
includes taxes & fees
Sep 23 - Sep 24
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
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 Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Lovely property in a beautiful setting. Really enjoyed the large rooms and the location for exploring North Fork."
Jessica 2-night trip
Posted 4 hours ago
The Shoals Suites and Slips

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
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Look no further and take a look at our great range of rental properties in Southold!

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 home 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.