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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (279 reviews)
"Great place!"
United States
Christine
$452 nightly
The price is $516
Aug 6 - Aug 7
Total with taxes and fees
Cliffside Resort Condominiums
Sun loungers, beach towels

2. 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.
$336 nightly
The price is $384
Sep 1 - Sep 2
Total with taxes and fees
Aqua Vista
Flat-screen TV

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$598 nightly
The price is $683
Aug 11 - Aug 12
Total with taxes and fees
North Fork Resort
Sun loungers, beach towels

4. 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.
$521 nightly
The price is $595
Aug 16 - Aug 17
Total with taxes and fees
The SandPiper
Beach

5. Harbor Heights

Harbor Heights
Pipes Cove
9.8 out of 10, Exceptional, (19 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
$452 nightly
The price is $516
Sep 3 - Sep 4
Total with taxes and fees
Harbor Heights
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.
$216 nightly
The price is $245
Sep 2 - Sep 3
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Beach

7. 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.
$594 nightly
The price is $679
Sep 2 - Sep 3
Total with taxes and fees
Beach Block Hideaway
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)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$485 nightly
The price is $554
Aug 10 - Aug 11
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
1 bedroom, bed sheets

9. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
$260 nightly
The price is $298
Aug 6 - Aug 7
Total with taxes and fees
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"⭐⭐⭐⭐⭐ 100/10 – An unforgettable romantic getaway! We had an amazing stay at this glamping site and spent two wonderful, romantic days here. The atmosphere was peaceful, cozy, and incredibly relaxing. Surrounded by nature, we enjoyed the fresh air, breathtaking sunsets, and quiet evenings that created memories we’ll always cherish. Everything was clean, comfortable, and thoughtfully prepared. The staff was exceptionally kind, welcoming, and always ready to help, which made our stay even more...
United States
Malika
$285 nightly
The price is $326
Aug 10 - Aug 11
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, bed sheets

11. Safari Tent Glamping,S9-CedarPt, East Hampton, NY

Safari Tent Glamping,S9-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"It was relaxing and beautiful - a perfect and affordable getaway from the city! Also great proximity to so many fun things."
United States
Carolyn
$260 nightly
The price is $298
Aug 6 - Aug 7
Total with taxes and fees
Safari Tent Glamping,S9-CedarPt, East Hampton, NY
Sun loungers, beach towels

12. 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.
$680 nightly
The price is $777
Aug 26 - Aug 27
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Dining

13. 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, (4 reviews)
"This was a great property. Very convenient to where we like to visit. It really had everything we needed for a great weeks stay."
United States
Sherri K.
$279 nightly
The price is $319
Aug 11 - Aug 12
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Sun loungers, beach towels

14. 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
$322 nightly
The price is $364
Aug 24 - Aug 25
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Beach nearby

15. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
$339 nightly
The price is $383
Aug 6 - Aug 7
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Coffee/tea maker, fridge, microwave, oven

16. 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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$288 nightly
The price is $326
Sep 2 - Sep 3
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
Beach nearby

17. 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
$262 nightly
The price is $296
Aug 6 - Aug 7
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Interior

18. 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.
$403 nightly
The price is $457
Aug 9 - Aug 10
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Smart TV, offices

19. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$643 nightly
The price is $693
Aug 9 - Aug 10
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach
Exterior

20. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
$646 nightly
The price is $738
Aug 6 - Aug 7
Total with taxes and fees
Lovely studio with AC in charming Sag Harbor
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Amazing hotel. New big rooms"
Julian 1-night trip
Posted 4 hours ago
The Bentley Hotel Southampton

Find out more about Southold

Everything you need to know about Southold vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southold vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southold vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southold vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southold. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southold in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $245 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southold rentals

At Expedia, we put the best Southold vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southold vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 115 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.