Southold Holiday Rentals

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Holiday Rentals in Southold

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (262)
"Lovely seaside accommodations. Very clean and comfortable. The location is perfect. The room was just a short walk from the beach. Just minutes away from downtown Montauk. Having a full kitchen is great."
The price is NZ$282
includes taxes & fees
3 Dec - 4 Dec
Windward Shores Ocean Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (166)
"Perfect family home"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (86)
"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! "
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!
10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"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. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Gorgeous private Hamptons house with pool and volleyball court
8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
Summer getaway
9.2 out of 10, Wonderful, (10)
"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...
Summer getaway
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (33)
"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!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (25)
"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."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (34)
"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...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
Contemporary home, newly built, heated pool and hot tub, large deck and...
9.4 out of 10, Exceptional, (8)
"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!!"
Contemporary home, newly built, heated pool and hot tub, large deck and...
70 Year old cottage on 2.8 acres, stunning views and sunsets
8.4 out of 10, Very good, (6)
"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!"
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
10.0 out of 10, Exceptional, (17)
"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."
Private 2.1 acre gated home with heated pool and tennis & pickleball court
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, (22)
"The house was as advertised, a perfect size for me and my sister. The yard was amazing with a beautiful view and really comfortable chairs to hang out in! Lori was so helpful and communicative. I had absolutely no problems reaching her when I had a question! Would return to this house for sure!"
Location and views! Located directly on Shinnecock Bay!
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, (11)
"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...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
Sag Harbor Suite by the Beach
8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
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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Other types of properties in Southold you may be interested in

The Shoals Suites and Slips
3.5 star property
9.4 out of 10, Exceptional, (130)
"Our room was close to the road and very noisy. Also we found ants in the kitchenette in the middle of the night. "
The price is NZ$371
includes taxes & fees
8 Dec - 9 Dec
The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (1026)
"Kind staffs!"
The price is NZ$149
includes taxes & fees
8 Dec - 9 Dec
Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (892)
"Everything was satisfactory"
The price is NZ$135
includes taxes & fees
24 Nov - 25 Nov
Pier Blue Inn Old Saybrook - Essex
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.
Beautiful view of the beach with palm trees

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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.