Villa vacation rentals in Chester

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Top-rated villa rentals in Chester

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Superhost

A collage featuring four aspects of the home. The top left displays a cozy living area with a fireplace and comfortable seating. The top right shows a hot tub surrounded by a wooden fence. The bottom left highlights a retro arcade setup with colorful lighting. The bottom right features a dining table set for a meal.

Villa in Kerhonkson

4.89 out of 5 average rating, 106 reviews

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!

Top guest favorite

Villa in Newburgh

5 out of 5 average rating, 74 reviews

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!

Guest favorite

A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.

Villa in Bloomingburg

4.84 out of 5 average rating, 79 reviews

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 the George Washington Bridge, 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!

Top guest favorite

Villa in Kerhonkson

4.97 out of 5 average rating, 281 reviews

Peaceful Forest Villa Escape w Private Yoga Studio

Nestled at the edge of the forest, Villa blends peaceful seclusion with refined comfort. Wake to birdsong, stretch in the private yoga studio or gather for movie night in the home theater. Large windows invite natural light and views of the trees, while indoor spaces flow naturally into the surrounding landscape. The open-concept living area is ideal for sharing meals or conversation. Whether you’r seeking stillness, inspiration, or connection, this space welcomes all with care and intention

Guest favorite

An aerial view of the property reveals a spacious lawn surrounded by manicured gardens and trees. The charming farmhouse is visible along with a patio area, swimming pool, and additional buildings, set against a backdrop of vibrant greenery under a clear blue sky.

Villa in Putnam Valley

5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Escape the city and step into luxury living at Bird Haven Farmhouse, a stylish retreat with all the amenities of a luxury hotel at your fingertips, while in a totally private villa setting. Designer details thru out this 3-Bedroom home: perfect for a summer or winter holiday, while having all the elements needed for a work-from-home set up. The former home of an artist and photographer, Bird Haven's manicured gardens and pool are the perfect setting for your retreat, or as a film location.

Guest favorite

An aerial view of a spacious property shows a two-story house surrounded by lush greenery and manicured lawns. A gravel driveway leads to the garage, and the outdoor deck is visible on one side, offering a serene environment amidst the trees.

Villa in Wallkill

4.98 out of 5 average rating, 45 reviews

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!

Villa in Monroe

4.71 out of 5 average rating, 96 reviews

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

A modern villa is set against a serene backdrop, featuring large windows that reflect the landscape. A small bridge leads over a private fishing pond, while trees line the property, inviting a peaceful atmosphere. Bright red doors stand out against the neutral exterior.

Villa in Port Jervis

4.65 out of 5 average rating, 65 reviews

Mountain Getaway by Legoland and Delaware River

Escape to our modern 6-bedroom, 3-bathroom villa, set on 3.2 acres of landscaped land with a private fishing pond. Enjoy the sleek and stylish interior, fully stocked kitchen with stainless steel appliances and granite countertops. Relax on the expansive deck while taking in the picturesque surroundings. Conveniently located near Legoland and Delaware River for outdoor activities. Experience the perfect blend of style, comfort, and nature all in one place!

Guest favorite

Two wooden chairs are positioned on a porch, providing views of the serene lake and lush greenery beyond. Natural light filters through the open space, with clouds reflective on the water's surface. The area is framed by decorative wood paneling, creating a cozy atmosphere.

Villa in Roscoe

4.94 out of 5 average rating, 16 reviews

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.

Guest favorite

The exterior of a modern home is presented amidst lush greenery, featuring a spacious wrap-around deck illuminated by warm lighting. An oversized hot tub is located on the deck, surrounded by natural rock formations and trees, creating a relaxed outdoor setting.

Villa in Tuxedo Park

4.95 out of 5 average rating, 86 reviews

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.

Top guest favorite

A spacious bedroom features a king size bed against a wall with large windows offering pleasant views. Two green chairs are positioned around a small table, creating a cozy seating area. Light wood accents on the ceiling enhance the room's airy feel.

Villa in New Paltz

5 out of 5 average rating, 14 reviews

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.

An airy great room features a striking red accent wall, complemented by wooden beams and large windows allowing natural light to fill the space. A stylish black sofa is positioned near a fireplace, with a collection of plants and bookshelves adding to the decor.

Villa in Newburgh

4.74 out of 5 average rating, 19 reviews

Exquisite Modernism overlooking the Hudson

Beautiful contemporary glass house in Balmville overlooking the Hudson River. Decadently and stylishly appointed with exquisite antiques and mid-century furnishings. An entertainers kitchen, sprawling decks, and panoramic views make this place an entertainers dream, or the perfect retreat just 90 minutes from NYC.