Luxury Hotels in Southold, New York

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Southold Luxury Hotels

Tonight
Jul 19 - Jul 20
Tomorrow
Jul 20 - Jul 21
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Top Southold Luxury Hotels

Frequently asked questions

Are you looking for a luxury hotel for your stay in Southold?
Use Expedia to help you arrange a flight to East Hampton, NY (HTO) airport or Westhampton, NY (FOK-Francis S. Gabreski) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Southold has to offer. Southold has some interesting things to see and do including Sparkling Pointe and Croteaux Vineyards, so you might want to take in the local sights during your visit.
What's the best high-end hotel in Southold?
Vine & Sand is a luxury B&B with a private beach and a seasonal outdoor pool, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in Southold?
Planning for the weather is an important factor for making your trip to Southold a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.
What's there to see and do in Southold?
Experience Southold with a stop at Sparkling Pointe, Croteaux Vineyards, and Osprey's Dominion. If you have extra time while you're in the area, you might want to stop by Sannino's Bella Vita Vineyard and Custer Institute and Observatory.
How can I get around Southold?
It's easier to get around town in style when you know your options. If you want to venture outside of the area, hop on a train at Southold Station.