
Villa vacation rentals in Chester
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Top-rated villa rentals in Chester
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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!

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!

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.

Harmony House - A Luxury Retreat Back in Time
Pamper yourself in our beautiful Victorian estate. Built in 1850 and home to one of the most famous racehorses in history, Harmony House is kept in pristine condition & updated w/ modern comforts. Designated a Historic home but running on Solar energy our country-style home offers 7 bedrooms, 4.5 baths, large living spaces & dining areas, chefs kitchen, fireplaces, pool, pool house, patio, grill, lawns & gardens. Walking distance to cafes & shops in Chester & only 50 miles to NYC!

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.

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.

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.
Popular amenities for Chester villa rentals
Private villa rentals

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

Harmony House - A Luxury Retreat Back in Time

The Carriage House on Hudson

Goshen Retreat w/ Hot Tub & 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

Ultra Modern Private Oasis with River Views
Luxury villa rentals

Harmony House - A Luxury Retreat Back in Time

Exquisite Modernism overlooking the Hudson

The Carriage House on Hudson

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Country home with rock climbing gym, pond & creek.

Goshen Retreat w/ Hot Tub & Fire Pit near Legoland

Serene and Peaceful - Surrounded by Nature

Lakefront Estate Film Location Sunset Views
Villa rentals with a pool

Private Room with a stunning balcony & view

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Beautiful farmhouse nature escape 90 min from NYC

Serene and Peaceful - Surrounded by Nature

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

Nightly prices starting at
Chester vacation rentals start at $1,371 CAD 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
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Central Park Zoo
- Yankee Stadium
- Mountain Creek Resort
- Citi Field
- United Nations Headquarters
- Grand Central Terminal
- Bethel Woods Center for the Arts
- Rye Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Bushkill Falls
- Radio City Music Hall
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve
- Bronx Zoo
- Thunder Ridge Ski Area