Find hotels in Wingdale, NY from $82

For visitors to Wingdale, the best area to stay is directly within the resort property itself, as Wingdale is primarily known for this singular, expansive destination.The resort is designed as a self-contained retreat, offering a variety of accommodations, dining options, and recreational activities all within its grounds. You'll find everything from a large, serene lake for water activities to extensive hiking trails winding through the natural landscape. The property also features tennis courts, a golf course, and a large indoor fitness center with high-end equipment and group classes.Couples looking for a relaxing escape will find the resort particularly appealing. The spacious grounds provide ample opportunities for quiet walks, spa treatments, and enjoying meals with scenic views. Many accommodations offer private balconies or patios, enhancing the sense of seclusion and tranquility.For families, the resort offers numerous activities to keep everyone engaged, including a large outdoor pool area and organized recreational programs.

While Wingdale doesn't typically serve as a primary destination, the best times to visit the surrounding Dutchess County area are during the spring, summer, and fall months, from May through October.Late spring and early summer, particularly May and June, offer pleasant weather for outdoor activities. The rolling hills are lush, and local farms begin to open for produce and flower picking. It's an excellent time for couples interested in scenic drives and visiting local vineyards or small towns without the peak summer crowds.For those seeking the warmest weather and a full range of outdoor options, July and August are ideal. This period is superb for families looking to enjoy nearby lakes, hiking trails, and outdoor dining experiences. Many seasonal attractions are fully operational, offering plenty of activities for all ages.The fall, especially September and October, is arguably the most picturesque time to visit due to the stunning foliage. The cooler temperatures make it comfortable for exploring the numerous hiking trails and enjoying the vibrant autumn colors.

With Expedia, you earn OneKeyCash™* on eligible Wingdale hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.