Luxury Hotels & Resorts 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 need 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 travellers 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 temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.

Experience Southold with a stop at Sparkling Pointe, The Old Field Vineyards and Corey Creek Winery. 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 the area, hop aboard a train at Southold Station.