Villa holiday rentals in Chester

The Falls

Welcome to The Falls. We are located on The Edge of the waterfalls in the center of town in Woodstock. Wake up to the sounds of the falls, sit on the porch and immerse in nature. There is an open kitchen to cook, a dining area to entertain and a living room with large windows that will give you a little glimpse of heaven on earth. You are surrounded by tranquility. This is an experience that you will remember for a life time. Close to all restaurants, stores and hiking trails. Just BE in nature.

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!

Spiti Helios: luxury retreat w/hot tub & pool

Καλώς Ορίσατε (welcome) to the beautiful Hudson Valley surrounded by distilleries, wineries (Magnanini Winery 6 minutes away 😉), spas, nature, and whatever your heart desires. Come zen out in this luxurious gem nestled on nearly 2 acres of privacy~did we mention the hot tub? *2-3 night stays get a discounted rate *Please enter all daytime visitors and overnight guests at time of inquiry. For early / late check out options check “other details”. Now let’s kick back and enjoy the Gunks!

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!

Country home with rock climbing gym, pond & creek.

This country-side home is the perfect retreat whether to work from home or enjoy time off with family and friends surrounded by nature. The home has beautiful creek, pond with Koi fish, local hiking trails only minutes away from the property, and a covered outdoor eating area. Enjoy the homes private rock-climbing gym, outdoor swing, fully equipped kitchen, pool table, towel warmers, and good espresso machine. Every room has a dedicated work space with high speed internet.

7 bdrm 5000sf luxury 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]

Awesome Country Retreat - 4BR - Private & Peaceful

Just an hour from downtown NYC, my spacious country home offers the perfect retreat for families or friends. Whether you're soaking in the jacuzzi-style bath, or enjoying the warm grass beneath your feet, this property is designed for ultimate relaxation with loved ones. Secluded and private, yet only a 5-minute drive to the charming town of Monroe, this home offers both tranquility and convenience. Professionally cleaned and managed for your peace of mind

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.

Villa Retreat: Yoga Studio, Theater, EV Charger

Multi-level forest villa retreat in the Gunks, perfect for wellness escapes, creative retreats, or group getaways. Enjoy a private yoga studio, 110" home theater, EV charger, handmade furnishings, Casper and Nectar premium mattresses, and inspiring original art. Surrounded by forest with decks, private nooks, and cozy lounges, this beautifully designed home blends boutique comfort with spacious indoor-outdoor flow.

Tuxedo Hilltop Retreat with a Large Hot Tub

Welcome to our peaceful getaway home set in the stunning Sterling Forest Park in the Hudson Valley, only an hour from New York City. Enjoy the tranquil outdoors, the oversized hot tub, the wrap-around balcony, and the spacious deck. Relax in a great room overlooking the forest and unique natural rock formations. And for the ski enthusiasts our home is only 10mi or an easy 20 min drive to Mt. Peter Ski Area.

Country House, Mountain Views, Dine, Bike, & Hike

Welcome to Enthusiastic Spirits Main House. World class climbing, biking, swimming, and endless exploring. The Hudson Valley is dotted with great restaurants, craft wineries and distilleries, art galleries, local crafts and historic attractions. New Paltz, Mohonk and Minnewaska are just 10 min away. Simply, a great place to stay and play. We no longer have a hot tub available on this property.