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

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!

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!

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.

Serene and Peaceful - Surrounded by Nature
Tastefully decorated,spacious,open concept,stylish,fine art,luxurious furnishings,4 bedroom,2.5 baths,in Garrison. Stunning views of Hudson Valley. Blue stone patios, in-ground salt water pool, teak furniture. Private,quiet,acreage,verdant landscaping. *Discounts available for extended stays. *Summer/holiday weekend bookings are a minimum of 3 nights.
Popular amenities for villa rentals in Chester
Private villa rentals

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

The Carriage House on Hudson

Goshen Retreat w/ Fire Pit near Legoland

Lakefront, newly renovated home in the Catskills

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

Villa Retreat: Yoga Studio, Theater, EV Charger

Awesome Country Retreat - 4BR - Private & Peaceful

Ultra Modern Private Oasis with River Views
Luxury villa rentals

Charming Country Home with Hot Tub, Pond & Creek

Lakefront Estate Film Location Sunset Views

Luxury 6BR Villa Escape Near Port Jervis New York

Exquisite Modernism overlooking the Hudson
Villa rentals with a pool

Contemporary Lake Front - 5 Acres!

Private Room with a stunning balcony & view

Goshen Retreat w/ Fire Pit near Legoland

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Pool and tennis court, 5 bedroom beautiful home

Best pool in town Davos
Quick stats about villa rentals in Chester

Nightly prices starting at
Chester holiday rentals start at £731 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
- Long Island Holiday rentals
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- 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
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Grand Central Terminal
- New York Public Library Main Branch
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Empire State Building
- Radio City Music Hall
- Statue of Liberty
- Bethel Woods Center for the Arts
- Bushkill Falls
- USTA Billie Jean King National Tennis Center
- The Metropolitan Museum of Art
- Thunder Ridge Ski Area
- Astoria Park
- One World Trade Center
- Bronx Zoo




