Southold Holiday Rentals from €157: Search Short-Term Rentals

Check Southold holiday rental availability

Holiday Rentals in Southold

"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."

includes taxes & fees

2 Dec - 3 Dec

"Stove it’s not efficient and refrigerator blocked with the corner of wall"

"Perfect family home"

"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "

"Great space and location. We loved the house and enjoyed our stay. "

Beach nearby, sun-loungers, beach towels

"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "

"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "

"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "

"Enjoyed this house in a great location. It was perfect for attending a family wedding!"

"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...

"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"

"We spent the weekend at the shore to celebrater my wife's 70th Birthday. The accommodations were fabulous and everyone enjoyed the home, the view and the location. Thank you to our host Laura."

"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...

Microwave, oven, stovetop, coffee/tea maker

"This house was great! Exactly as pictured. Only callout is the outdoor furniture by the pool needs a really good spray down/wash. Everything else was absolutely great!!"

"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"

"With a baby we needed a place with enough entertainment, so we didn’t have to go out much. This place has ALL of that and more. We loved it. We cooked, grilled, swam, played tennis, pickleball, ping pong, pool; all at the house. It was perfect."

"We enjoyed our stay. The location was great and the owner was available for questions. "

"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...

"Ken was great and easy to work with. The house was nice and perfect for our stay!"

"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Other types of properties in Southold you may be interested in

"The Shoals is really such a cute place. The rooms are spacious and very clean. My sisters and I stayed here for the second time in November. Last time I stayed during the week and it was very quiet. However this time we had someone staying next to us and you can hear the TV like it’s in your room as it is up against your bed wall and just someone walking was loud. Thankfully they didn’t keep the TV on all night. When you arrive at the Shoals there is someone at the front desk but they leave by...

includes taxes & fees

25 Dec - 26 Dec

Indoor pool, open 9:00 AM to 9:00 PM, pool loungers

"My mattress was less than good and needs to be replaced. Otherwise, the facility was clean and reasonable with a good breakfast."

includes taxes & fees

11 Dec - 12 Dec

"Everything was satisfactory"

includes taxes & fees

1 Dec - 2 Dec

Find out more about Southold

Everything you need to know about Southold holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southold holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southold holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southold holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southold holiday rentals we have selected for you start as low as €157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southold rentals

At Expedia, we put the best Southold holiday 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 holiday.

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.

Recent reviews of Southold properties

5/5 Excellent

"My mattress was less than good and needs to be replaced. Otherwise, the facility was clean and reasonable with a good breakfast."

A verified traveller stayed at Quality Inn Old Saybrook - Westbrook

Posted 2 days ago

5/5 Excellent

"The hotel is majestic and on the water with beautiful views. The staff was without exception incredibly attentive and friendly- from Sara and Matthew at the front desk to the gentleman who helped us with the fireplace to Mike and the other valets who took care of the car. Wonderful experience!"

A verified traveller stayed at Madison Beach Hotel

Posted 6 days ago

Frequently asked questions

Can I find a holiday rental in Southold?

Yes, there are holiday rentals close to the most popular sights in Southold, 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 Drive,40ft Heated Pool,Beach,Family Fr: 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 129 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?

Horton Lane Beach and Horton Point Park 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Southold

Check Southold holiday rental availability

Holiday Rentals in Southold

Windward Shores Ocean Resort

Cliffside Resort Condominiums

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Beautiful Family Home Nestled In The Heart Of Sagaponack

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Gorgeous private Hamptons house with pool and volleyball court

Summer getaway

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

Contemporary home, newly built, heated pool and hot tub, large deck and...

70 Year old cottage on 2.8 acres, stunning views and sunsets

Private 2.1 acre gated home with heated pool and tennis & pickleball court

Location and views! Located directly on Shinnecock Bay!

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

Sag Harbor Suite by the Beach

Other types of properties in Southold you may be interested in

The Shoals Suites and Slips

Quality Inn Old Saybrook - Westbrook

Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Recent reviews of Southold properties

Quality Inn Old Saybrook - Westbrook

Baron's Cove

Sound View Greenport

Saybrook Point Resort & Marina

The Harbor Front Inn

Water's Edge Resort & Spa

The Bentley Hotel Southampton

Madison Beach Hotel

The Sagaponack

Frequently asked questions