Photo by Benny Goh
Search Chalets in Southold
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Chalets in Southold
No exact matches found, but these alternatives could be just right
Recommended hotels in Southold
The Shoals Suites and Slips
Southold
9.6 out of 10, Exceptional, (224)
"Great quick stay"
Jasmine T
The price is SAR 620
SAR 708 total
includes taxes & fees
21 Dec - 22 Dec
Vine & Sand
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
Sandra
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
Jessica P.
The price is SAR 1,336
SAR 1,745 total
includes taxes & fees
4 Jan - 5 January 2026
Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
Anonymous traveler
The price is SAR 2,252
SAR 4,409 total
includes taxes & fees
11 Dec - 12 Dec
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
Mark L.
The price is SAR 1,218
SAR 1,593 total
includes taxes & fees
4 Jan - 5 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is SAR 1,218
SAR 1,593 total
includes taxes & fees
4 Jan - 5 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is SAR 1,336
SAR 1,745 total
includes taxes & fees
4 Jan - 5 January 2026
The Roundtree, Amagansett
Amagansett North
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
adam
The price is SAR 2,231
SAR 2,676 total
includes taxes & fees
1 Jan - 2 January 2026
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.
Top Southold Hotel Reviews
Hilton Garden Inn Riverhead
10/10 Excellent
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Southold
- Vacation Homes in Southold
- Cottages in Southold
- Apartments in Southold
- B&B in Southold
- Villas in Southold
- Condo Rentals in Southold
- RV Parks in Southold
- Motels in Southold
- Farmstay in Southold
- Aparthotels in Southold
- Resorts in Southold
- Inns in Southold
- Cabin Rentals in Southold
- Houseboats in Southold
- Guest Houses in Southold
- Hostels in Southold
- Residences in Southold
- Hotels