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, (298)
"Loved the balcony view….wrong season for swimming but pool looks inviting"
Windward Shores Ocean Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (243)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
The price is AU$459
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$407
includes taxes & fees
19 Oct - 20 Oct
Shoreline Oasis
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is AU$594
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (33)
"Enjoyed our stay"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
The price is AU$495
includes taxes & fees
15 Oct - 16 Oct
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Large Charming Historic House close to Beaches
9.8 out of 10, Exceptional, (33)
"Great place and location. There was 8 of us and plenty of space and beds!"
Large Charming Historic House close to Beaches
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (140)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
10.0 out of 10, Exceptional, (15)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is AU$512
includes taxes & fees
20 Oct - 21 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is AU$257
includes taxes & fees
19 Oct - 20 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$257
includes taxes & fees
15 Oct - 16 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
1-bedroom cottage with Grove Beach 🏖️ access.
9.4 out of 10, Exceptional, (32)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AU$281
includes taxes & fees
20 Oct - 21 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is AU$1,416
includes taxes & fees
17 Oct - 18 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
The price is AU$2,227
includes taxes & fees
11 Nov - 12 Nov
Work and Play Special! Extended Stay Discount
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
9.8 out of 10, Exceptional, (109)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (75)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (192)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is AU$1,996
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
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

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, 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 favourite 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 depend 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 AU$257 per night. Entering your travel dates in the search wizard might find you 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. 

Frequently asked questions

Can I find a holiday rental in Southold?

Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Southold?

With 126 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?

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 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.