Villa vacation rentals in Chester

Catskills Sunset Estate, Hotub, Pond, 21+ppl

Getaway at Sunset Mountain Estate -enjoy the luscious yards, amenities and natural privacy! Several bedrooms, and family game room. Spend time at the pond in your own island gazebo or grab a beer in BBQ marquee as the grill works its magic. Don’t miss the large Hottub, swingset for kids, volleyball, firepit+ 2 acres of serenity! ✔ Plenty of Bedrooms of all types ✔ Fully Equipped Kitchen ✔ Pond with small Island ✔ Large Hot Tub ✔ Pool Table ♛ Guest Favorite ♛ One of the most loved Airbnbs!

Gilded Cage Escapes | Hidden Playroom for Adults

Gilded Cage Escapes offers Boutique vacation suites, riverfront seclusion, sensory speakeasies with Industrial playrooms for consenting adults. Our spaces are design-forward sanctuaries for your most intimate experiences. "The Aviary Lounge" is an exclusive riverfront suite for couples featuring an art-deco playroom for adults. Gilded Cage Escapes was built for everyone. We celebrate and enthusiastically welcome guests of all ethnicities, skin tones, gender identities, and sexual orientations.

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub|Pool

Enjoy a luxury nature escape at Boho Chic Villa, under 2 hours’ drive from New York City. This cozy home offers three bright bedrooms, an elegant full kitchen, and unmatched outdoor space. Take a splash in the pool, soak in the hot tub, or make s’mores around the fire pit. Your stay is sure to be an extraordinary experience for the whole family. 6 Min Drive to Minnewaska State Park 8 Min Drive to Kelder’s Farm 10 Min Drive to Stony Kill Falls Experience Kerhonkson With Us & Learn More Below!

Ultra Modern Private Oasis with River Views

Step into your brand new, ultra-modern secluded oasis with picturesque views of the Hudson River and Valley. The Balthus Haus was designed and built with sheer comfort, stylish aesthetics, and progressive functionality as the guiding tenets. Nestled high into the hillside the Haus maximizes 360 degrees of privacy and is surrounded by nature. Inviting and pleasant all year round with central AC and radiant heated floors throughout the living areas. Easily get away from NYC only 1.25 hours away!

Hudson Valley Haven in Hopewell

Relax at Beekman lodging close to many riches of Hudson Valley, only 60mi from NYC. The hot tub runs all year round and the Heated pool is a delight to win hearts from May thru October. Our 3 bdrm home, sleeping 8 guests, is within 20mi of Dia Beacon to the west, Fishkill Ridge trail to the north, snow sports at Thunder Ridge to the east, and the breathtaking beauty of Wappinger waterfalls to the south. We are also a stone’s throw from multiple farms where apple picking and hayrides abound.

Beautiful farmhouse nature escape 90 min from NYC

Relax with the whole family at this peaceful retreat. Feels far more remote than the short drive (or Metro North ride) from the city would suggest! As you make your way down the long tree-lined private driveway and see the classic house and barn, you can feel the atmosphere shift. Come enjoy our spacious farmhouse with antique charm and modern kitchen/amenities. Walk the path around the property, wander the woods, watch the sunrise over the valley, or go apple picking or skiing nearby.

Lux Catskills Villa-3 hiking trails with 4br 4bath

The Catskill Park Manor is a luxurious historical abode designed by renowned architect Peter Pennoyer and featured in Architectural Digest, on Upstate House magazine, Forbes Magagine, on two tv shows and was the location for Urban Outfitters 2020 Summer photo shoot. Hike on 131 acres of private trails, go to the famous swimming hole 3 just a three minute drive, drive four minutes away to the Russian Mule brewery where there is live music most weekends! ask us about local events!

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6BR villa, a serene mountain retreat with scenic views. This peaceful getaway is perfect for families and groups. Located approximately 1 hour from New York city, it offers comfortable interiors, a well-equipped home, and ample outdoor space. Explore nearby hiking trails and relax in a tranquil setting just minutes from local attractions. Unwind and experience nature in every direction. Your peaceful mountain escape awaits—BOOK NOW FOR A SERENE GETAWAY!

7 bdrm 5000sf Grand Pool Villa|Hottub|Sauna|Movie

Our huge 5000 sq ft, 7 bedroom, 4.5 bathroom home which sleeps 20 guests, is located very centrally in the heart of Poconos.Enjoy the amazing flat backyard with brand new OUTDOOR PRIVATE INGROUND POOL (20x40 size, 3’-6’ deep) Tastefully decorated, this home has everything you need to enjoy your time whether you want to relax, play a game of poker, billiards, or cook a family meal at our oversize kitchen for a large group! [INGROUND POOL CLOSE FOR THE SEASON]

Lakefront, newly renovated home in the Catskills

Casa Julia is the perfect NY getaway; Enjoy access to Tennanah Lake, one of the most seek after private lakes in the Catskills. This newly renovated home has stunning lake views, well curated interior design and high speed internet. The perfect place for a weekend getaway or a work from home paradise. Nearby hikes, rivers, golf, tennis and ski mountains will thrill those with adventurous spirit. Grab paddle boards and enjoy a magical sunset on the lake.

Beautiful 5BR Hudson Valley Villa

RELAX AND PLAY in beautiful updated sun-drenched 5 BR/3 BA home with Great Room, modern kitchen, yoga sunroom, and spa-like primary BA w 6-foot soaking tub. Amazing outdoor space w giant pool, patio, firepit, grill. Max occupancy is 10 people. No Pets. A modern oasis in the Hudson Valley near hiking, rock-climbing, road and gravel cycling, skiing, apple-picking, antiquing, bird-watching and other fun seasonal activities.

Goshen Retreat w/ Fire Pit near Legoland

Set among the rolling hills of Goshen, this historic estate blends rustic charm with a touch of luxury, creating a peaceful getaway from city life. Just 19 miles radius distance from West Point and minutes from Legoland, this beautifully preserved home places you at the center of the Hudson Valley’s best attractions. Be sure to check out the Brotherhood Winery, the oldest winery in America, for a memorable local experience!