Southold Vacation Rentals from ￥10,740: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Southold has to offer?

Hamptons Retreat : You might want to consider this vacation home rental near Southold, which offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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Vacation Rentals in Southold

Enjoy a panoramic ocean view from the comfort of this room, featuring a dining table, seating area, and sliding glass doors to the outdoor patio.

"Easy checking in and out Easy access few steps to beach from first floor unit "

￥76,041 total

includes taxes & fees

Jul 27 - Jul 28

Stunning beachfront residential area with multi-story buildings and a central park.

"Very nice, clean and cosy place! Highly recommend!"

￥97,799 total

includes taxes & fees

Jul 28 - Jul 29

Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

"Great place! Great communication with property owner!"

￥95,294 total

includes taxes & fees

Jul 27 - Jul 28

Simple, functional room with a single bed and a window with curtains.

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

"Loved our stay and will be back"

Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"

Relax in this spacious living area with a high ceiling, large windows offering views of the surrounding trees, and a comfortable seating arrangement.

"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "

Enjoy a serene beach experience with access to the ocean and a sailboat visible in the distance.

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

￥30,097 total

includes taxes & fees

Jul 21 - Jul 22

Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

"The house and town were adorable. The space was the second floor. It was clean and and comfortable. "

￥39,226 total

includes taxes & fees

Jul 21 - Jul 22

Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

"Close to the shore and the heart of Old Saybrook. The house is very comfortable."

￥96,132 total

includes taxes & fees

Aug 2 - Aug 3

Enjoy a serene beach experience with access to the ocean and a picturesque sailboat in the distance.

"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "

￥29,071 total

includes taxes & fees

Jul 30 - Jul 31

Enjoy a serene beach experience with access to the ocean and a picturesque palm tree.

"I love everything about this property. Excellent response from host. Excellent cleanliness of place. OVERALL TOP EXPERIENCE. 1000 PERCENT will be back."

￥28,262 total

includes taxes & fees

Jul 21 - Jul 22

Enjoy a serene meal on the deck overlooking the tranquil waters of East Hampton, New York.

"Very nice and relaxing stay in Springs! "

Relax by the serene pool surrounded by lush greenery and comfortable seating.

"It was a great stay"

Relax by the serene pool surrounded by lush greenery and shaded lounge chairs.

"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"An absolute perfect home for a family looking to enjoy"

Relax by the serene pool surrounded by lush greenery.

"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."

￥141,622 total

includes taxes & fees

Jul 27 - Jul 28

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Top Southold Hotel Reviews

Greenview Inn Riverhead

10/10 Excellent

"Friendly staff Conveniently located Clean!"

Saybrook Point Resort & Marina

10/10 Excellent

"I always enjoy stopping at the Saybrook Inn and Spa. The front desk gentleman were very nice and welcomed me back. We arrived almost at restaurant closing time and our server was accommodating and kind. The hotel is pet friendly and the breakfast wait staff were great. Look forward to our next visit."

Hotel Indigo East End by IHG

10/10 Excellent

"I love the convenience of having a bar/restaurant right in the hotel. The pool is gorgeous. I love that it’s a small hotel. The complimentary breakfast is nice to have, and the hours it’s opened is great for people like me that like a little more sleep. This was my 2nd time here, and I look forward to going back. "

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"The hotel is lovely. By their own admission the owners have a notice saying excuse us whilst we renovate. The lodge was fine, we didn’t really notice it wanted much done. The car park was plenty, the room was spacious and comfy. Great views out the back. Convenient for the area, we really liked it. "

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:

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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?

Hamptons Retreat: You might want to consider this vacation home rental near Southold, which offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Southold?

With 128 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.

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Southold Vacation Rentals

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Vacation Rentals in Southold

Windward Shores Ocean Resort

Cliffside Resort Condominiums

Canoe Place Waterfront Residences

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Sag Harbor Suite by the Beach

NORTHFORK COTTAGE with POOL & HOT TUB

Hamptons Retreat

Fairy Tale Guest Cottage in Magic Garden by Pool

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

The Stern at Soundview · Beach+Ocean+Sunrise

Shoreline Oasis

adorable ranch in beach community

The Anchor at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise

Perfect Mid-Century Private Waterfront East Hampton Retreat!

Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

Walk to town, Bike to beach, Private pool oasis !

Southampton cozy cottage by the beach

Top Southold Hotel Reviews

Greenview Inn Riverhead

Saybrook Point Resort & Marina

The Bentley Hotel Southampton

Hotel Indigo East End by IHG

The Shoals Suites and Slips

Pier Blue Inn Old Saybrook - Essex

The Atlantic Hotel

The Pridwin Hotel

Hilton Garden Inn Riverhead

Find out more about Southold

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Frequently asked questions