Villa holiday 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
4.88 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!

Top Guest favourite
A modern black cottage is set against a backdrop of vibrant fall foliage. The home features multiple levels with an array of windows, allowing for natural light and views of the surrounding landscape. Lush green grass and garden areas frame the entrance.
Villa in Livingston Manor
5 out of 5 average rating, 40 reviews

Welcome to Shangri-Lew! An idyllic mountain escape

Stunning mountain-top villa on 26 acres and surrounded by 15k acres of state land in the pristine hamlet of Lew Beach, minutes from Livingston Manor and Beaverkill River. Panoramic 10+ mile views from two decks or massive great room with floor to ceiling windows. Huge professional kitchen with top of the line appliances. Beautifully furnished rooms. Indoor/outdoor tv's & fireplaces, outdoor shower, CAC, huge master spa, soaker tub, breathtaking grounds. Hiking, fishing, skiing, shopping near by.

Superhost
Villa in Ossining
4.65 out of 5 average rating, 23 reviews

Westchester Summer: Pool Pet Friendly Events Games

Spring and summer escape at The Westchester Manor, a spacious 5BR, 4BA Tudor for up to 13 guests, pet-friendly. Enjoy sunny days by the pool, unwind at the custom in-house bar, and relax with arcade games, pool table, Smart TVs, and fast Wi-Fi. Fully equipped kitchen and in-unit laundry included. Located under 1 hour from MetLife Stadium, East Rutherford, host of the FIFA World Cup 2026. Near Sleepy Hollow, Croton Gorge Waterfalls, and Bear Mountain. Events are welcome, message for more details!

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 favourite
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 favourite
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!

Guest favourite
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 Woodstock
4.84 out of 5 average rating, 81 reviews

Prime Woodstock Luxe 5BR-3Baths-Heated Ing Pool

Say hello to your perfect vacation home! Bright and airy Woodstock home with all the amenities you will need. Located only 2 minutes from the Village of Woodstock. Ski Belleayre, Hunter or Windham. 5-bedroom house w/3 full bathrooms located on private roadway perfect for walking & running around neighborhood. The house features heated(off for 2025) pool( still open) Hot-Tub, 3500sf outdoor deck with BBQ grill, fire pit, & large tranquil garden with privacy, Wood pellets burning fireplace.

Guest favourite
A tranquil winter scene depicts a classic farmhouse and a red barn surrounded by a blanket of fresh snow. A path is visible in the snow, leading toward the inviting buildings, and tall trees are present in the background, adding to the serene atmosphere.
Villa in Wingdale
4.88 out of 5 average rating, 17 reviews

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.

Guest favourite
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.

Popular amenities for Chester villa rentals

Quick stats about villa rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $1,314 AUD 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!

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