Southold Vacation Rentals from $205: Search Short-Term Rentals

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Our top choices for Southold vacation rentals

1. Cliffside Resort Condominiums

Greenport

Christine

$370 nightly

Sep 27 - Sep 28

Total with taxes and fees

2. North Fork Resort

Greenport

Lisa

$286 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

$373 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Aqua Vista

Pipes Cove

Kerri L.

$279 nightly

Oct 7 - Oct 8

Total with taxes and fees

5. The SandPiper

Pipes Cove

Timothy

$316 nightly

Sep 10 - Sep 11

Total with taxes and fees

6. Harbor Heights

Pipes Cove

Nigel

$278 nightly

Oct 5 - Oct 6

Total with taxes and fees

7. Beach Block Hideaway

Pipes Cove

Teresa C.

$366 nightly

Sep 7 - Sep 8

Total with taxes and fees

8. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

$313 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

East Hampton

Christina V.

$260 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

East Hampton

Michael H.

$260 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Clinton

JM B.

$208 nightly

Oct 5 - Oct 6

Total with taxes and fees

12. Seabreeze #3 Cozy Cottage steps to the beach

Hampton Bays

"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...

Anonymous traveler

$457 nightly

Sep 9 - Sep 10

Total with taxes and fees

13. Renovated Townhouse walk to all

Greenport

Melissa A.

$627 nightly

Sep 17 - Sep 18

Total with taxes and fees

14. Northfork Townhouse walk to all

Greenport

Beth R.

$695 nightly

Sep 10 - Sep 11

Total with taxes and fees

15. Charming Accommodations in the Hamptons

Sag Harbor

$469 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Westbrook Center

Donovan V.

$424 nightly

Sep 9 - Sep 10

Total with taxes and fees

17. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Flanders

James W.

$301 nightly

Sep 28 - Sep 29

Total with taxes and fees

18. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Wink V.

$285 nightly

Oct 7 - Oct 8

Total with taxes and fees

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

Greenport

Jeannette M.

$878 nightly

Sep 15 - Sep 16

Total with taxes and fees

20. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

$322 nightly

Sep 9 - Sep 10

Total with taxes and fees

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Top Southold Hotel Reviews

Zey Hotel

10/10 Excellent

"The manager, James was so helpful during our stay. We loved that there was parking and a lovely home base during our getaway in Greenport. We loved the Zen feel, garden and lounge where we could read and relax during our stay. Our room was cozy and cool!"

North Fork Resort

8/10 Good

"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. It’s a 45 min walk from the train station so if you’re coming from the city it’s not a convenient location and it’s off a busy road. The cottage did have lots of kitchen amenities and a grill which is great if you’re looking for some easy meals. The shower’s water pressure was great and the air conditioning was effective. Unfortunately you can’t open any windows because there are no screens in the windows and the area is buggy. Overall, the place was nice but the rooms are smaller than I expected and you’re far from everything (even the main reception and pool)"

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."

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 $205 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.

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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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Southold vacation home rental. It is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.

Southold Vacation Rentals

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Check prices for these dates

Our top choices for Southold vacation rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

4. Aqua Vista

5. The SandPiper

6. Harbor Heights

7. Beach Block Hideaway

8. American Beech in Greenport - Petite King Room 7

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

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

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

12. Seabreeze #3 Cozy Cottage steps to the beach

13. Renovated Townhouse walk to all

14. Northfork Townhouse walk to all

15. Charming Accommodations in the Hamptons

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

17. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

18. The gardners Cottage 1 mile from long Island Sound - pet friendly

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

20. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Find vacation rentals that suit your style

Top Southold Hotel Reviews

Zey Hotel

Find out more about Southold

Explore a world of travel with Expedia

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