Find luxury hotels in Southold, NY

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 The Old Field Vineyards, so you might want to take in the local sights during your visit.

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.

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.

Experience Southold with a stop at Sparkling Pointe, The Old Field Vineyards, and Croteaux Vineyards. If you have extra time while you’re in the area, you might want to stop by Sannino’s Bella Vita Vineyard and Mattebella Vineyards.

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.