Holiday Rentals in Southold
Holiday Rentals in Southold
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
North Fork Escape Near Wineries, Beaches And Hamptons
Beautiful Family Home Nestled In The Heart Of Sagaponack
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Airstream Art Studio Sculpture/Nature Preserve
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Beach House
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Beautiful 3 bedroom Residence in the Hamptons
70 Year old cottage on 2.8 acres, stunning views and sunsets
Location and views! Located directly on Shinnecock Bay!
Summer getaway
"Salt 'n' Lyme" - Walk to everything !
Patchogue River Retreat, 8 minute walk to West Beach
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Other types of properties in Southold you may be interested in
The Shoals Suites and Slips
Hilton Garden Inn Riverhead
Pier Blue Inn Old Saybrook - Essex
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 €161 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.