
Villa holiday rentals in Chester
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Top-rated villa rentals in Chester
Guests agree: these villas are highly rated for location, cleanliness and more.

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub
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. Soak in the hot tub, or make s’mores around the fire pit, visit local breweries/farms. 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!

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!

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!

Luxury 5BR Poconos Retreat | Ski, Lake & Resort
Nestled in a lush forest, this private, family-friendly sanctuary offers quiet seclusion with year-round resort fun. Enjoy countless activities, from skiing and tennis to indoor/outdoor pools and lakes. The airy home features a grand dining area for 14, a cozy wood fireplace, and a game room with a pool table. With 5 plush bedrooms and spa-like baths featuring a freestanding tub, there’s space for everyone. From forest views to resort amenities, experience the perfect getaway for any season!

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.

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.

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!

Charming Country Home with Hot Tub, 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.

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.

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!

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.

Luxury 6BR Furnished Estate on 7 acres - 31+ days
The Farm's Estate Home, 7 miles from NYC, sits perched on a private, peaceful hill above a gorgeous 7-acre certified-Organic farm. 31 day stay minimum. Get in touch via our Closter Farm contacts with ANY requests. The spacious, gracious funky Estate home with a giant private pool and Park Avenue-sized rooms sits inside the fence of a private, Oasis-like estate.
Popular amenities for villa rentals in Chester
Private villa rentals

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Goshen Retreat w/ Fire Pit near Legoland

Luxury 5BR Poconos Retreat | Ski, Lake & Resort

Lakefront, newly renovated home in the Catskills

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

Ultra Modern Private Oasis with River Views

Tuxedo Hilltop Retreat with a Large Hot Tub
Luxury villa rentals

Luxury 6BR Villa Escape Near Port Jervis New York

Charming Country Home with Hot Tub, Pond & Creek

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Goshen Retreat w/ Fire Pit near Legoland

Luxury 5BR Poconos Retreat | Ski, Lake & Resort

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

Lakefront Estate Film Location Sunset Views

Hillside villa with 9-mile lake views
Villa rentals with a pool

Contemporary Lake Front - 5 Acres!

Private Room with a stunning balcony & view

Best pool in town Davos

Beautiful 5BR Hudson Valley Villa
Quick stats about villa rentals in Chester

Nightly prices starting at
Chester holiday rentals start at £693 per night before taxes and fees

Verified guest reviews
Over 40 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chester rentals

4.9 Average rating
Chester stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Bronx Zoo
- United Nations Headquarters
- Rockefeller Center
- Brooklyn Bridge
- Citi Field
- Empire State Building
- Bethel Woods Center for the Arts
- Grand Central Terminal
- Bryant Park
- Statue of Liberty
- Radio City Music Hall
- Bushkill Falls
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art




