Villa vacation rentals in Chester

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Quick stats about villa rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at ﺩ.ﺇ3,452 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!

Top-rated villa rentals in Chester

Guests agree: these villas are highly rated for location, cleanliness, and more.

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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
4.88 out of 5 average rating, 112 reviews

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!

Superhost
A large red country villa is showcased alongside a well-maintained lawn, framed by trees. Large windows allow natural light to flow into the house. A stone path leads from the driveway to the entrance, which features a welcoming covered porch.
Villa in Monticello
4.68 out of 5 average rating, 68 reviews

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!

Top guest favorite
A contemporary living room features an 18-foot tall cathedral ceiling and a mix of stylish furnishings. Two couches are positioned around a circular blue rug, while a serene hammock hangs from the ceiling. A fireplace serves as the focal point, with plants adding life to the space.
Villa in Newburgh
5 out of 5 average rating, 86 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
Villa in Saw Creek
5 out of 5 average rating, 6 reviews

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!

An outdoor heated pool surrounded by a brick patio is framed by a wooden fence and lush greenery. Two lounge chairs are positioned nearby under a large umbrella, providing a relaxing space for sunbathing. The serene setting invites enjoyment of the fresh air.
Villa in Hopewell Junction
4.78 out of 5 average rating, 41 reviews

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.

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.

Villa in New Paltz
4.71 out of 5 average rating, 52 reviews

Unique Dome Home With Hot Tub & Piano, on 28 acres

One-of-a-kind Dome home on 28 acres of private forest. Surrounded by trees and wildlife, including deer, turtles, wild turkeys, birds, chipmunks, ground hogs, squirrels & rabbits. The house was recently updated with a new hot tub, baby grand piano, strong internet, house-wide sound system, good espresso machine & towel warmers. It has central heating and air-conditioning and a fully equipped kitchen. 10 min to town with restaurants, markets, rock-climbing and outdoor activities.

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
4.85 out of 5 average rating, 102 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 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!

Villa in Rock Hill
4.88 out of 5 average rating, 8 reviews

Spacious 8BR Catskills Cabin w/ Game Room & Deck

Escape to this spacious Catskills log cabin! With 8 bedrooms, 5.5 baths, all year round hot tub, game room, two decks, and large living areas, it’s perfect for groups and family getaways. Enjoy a full kitchen, central A/C, high-speed WiFi, washer/dryer, firepit, and peaceful forest views near parks, trails, lakes, ski resorts, and shops. Gather around the fireplace, explore nature, or relax on the deck. The perfect retreat to relax, connect, and unwind in every season.

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
4.95 out of 5 average rating, 20 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 historic estate features a grand facade highlighted by multiple gabled roofs and a striking red front door. Soft lighting glows from the windows, and lush greenery surrounds the stone steps leading to the entrance, emphasizing the peaceful atmosphere of the property.
Villa in Goshen
5 out of 5 average rating, 14 reviews

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!

Top guest favorite
Villa in Kerhonkson
4.97 out of 5 average rating, 324 reviews

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.

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