Compare Southold Chalets

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Featured Chalets in Southold

Guests staying at this chalet have access to laundry facilities, a garden, and barbecue grills.

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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.

Hotel Options in Southold

The Shoals Suites and Slips

61600 Main Rd Southold NY

$267 nightly

$302 total

Jun 2 - Jun 3

Total with taxes and fees

9.4/10 Exceptional! (275 reviews)

Vine & Sand

47100 New York 25 Southold NY

$456 nightly

$522 total

Jun 4 - Jun 5

Total with taxes and fees

9.8/10 Exceptional! (16 reviews)

The Atlantic Hotel

1655 County Road 39 Southampton NY

$221 nightly

$252 total

Jun 2 - Jun 3

Total with taxes and fees

7.2/10 Good! (1,002 reviews)

Chalets

Book the best chalets in Southold
Take a break from reality and kick back in a Southold chalet on your next vacation. Stay right in the middle of all the action, but feel like you’re miles away. Be as active or as relaxed as you want. Your chalet is truly yours. No one can tell you what to do on your chalet stay—and it’s the best way to enjoy a getaway.

Get the most from your chalet stay
You’ll make incredible new memories at chalets in Southold. They look great in your photos, with sunning backdrops and cozy touches like fireplaces and exposed beam ceilings. Wake up to light streaming through your big picture window and admire your incredible view. Don’t just look at the great outdoors, though. Get out there and experience all that Southold has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Southold chalet houses. Whether you use all those bedrooms for the kids or for your crazy crew, you can settle in quickly thanks to chalets’ convenient amenities. Whip up a meal in no time in the kitchen or kitchenette, or whip out your phone to call for delivery. Cozy up to the fire, or fire up the blender for some drinks. When you’ve got a chalet, it’s going to be good day.