Villa vacation rentals in Chester

5 out of 5 average rating, 33 reviews

The outdoor area features a seasonal custom pool surrounded by lounge chairs and shaded umbrellas. Lush greenery and trees create a natural backdrop, providing a serene and private setting for relaxation.

Villa in Mount Pocono

Modern Villa with Outdoor pool & Entertainments! 🎱

Enjoy this exquisite, one-of-a kind home with an outdoor custom pool right in the heart of the Poconos! Surround yourself with the natural beauty and nature; less than 15 mins. away from Mt. Airy Casino, Camelback, Kalahari Water Park, The Poconos Outlets, Shawnee ski area, Bushkill Falls, bike trails, horseback riding, hiking, lakes & restaurants. Enjoy this spacious home with built-in movie theater, pool table & bar/lounge & MORE! House features 4 levels! Pool is SEASONAL & not a heated pool

4.97 out of 5 average rating, 38 reviews

A modern kitchen features a spacious wooden island with eight bar stools. White cabinetry is complemented by open shelving adorned with plants and decorative items. Natural light streams through large windows, illuminating the wood flooring and stainless steel appliances.

Villa in Tobyhanna

Luxury Villa w/Hot Tub Movies Arcade Breakfast Gym

This Villa is an Oasis in the Poconos. Every detail of this home has been meticulously designed to bring your loved ones together while reconnecting you with nature & yourself. Our villa is packed w/amenities -Pergola over Hot Tub & Garden -Complimentary Breakfast, Popcorn, Cotton Candy, & Snowcones -Theater w/100" 4k Projector, 9.1 surround sound, & recliners -4-Player & Gun Arcade -Fire Pit w/16 Chairs -Outdoor Grill & Lounge -Giant Jenga & Checkers -Foosball, Air Hockey & Pool Table -Yoga Gym

4.91 out of 5 average rating, 175 reviews

A black wooden house is positioned dramatically over a cascading waterfall, surrounded by leafless trees. The structure features a spacious deck with wooden railings, offering scenic views of the flowing water below and neighboring houses visible in the background.

Villa in Woodstock

The Falls

A secret treasure in the heart of Woodstock. This waterfall escape is tucked up in the center of town with incredible privacy, a private deck overlooking the waterfalls and located on the entire first floor just up a flight of stairs of the main house. Enter through your own private deck overlooking the waterfalls. Walk to all the great restaurants, galleries and shops around Woodstock. A truly magical experience. amidst the trees on top of the waterfalls. The most sought after Airbnb in town.

4.89 out of 5 average rating, 97 reviews

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

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!

5 out of 5 average rating, 63 reviews

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

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!

4.79 out of 5 average rating, 63 reviews

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

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!

4.97 out of 5 average rating, 253 reviews

A serene bedroom features a spacious bed dressed in yellow and white linens, complemented by wooden accents and large windows. A jacuzzi tub is positioned nearby, and a ceiling fan hangs above, adding comfort to the inviting atmosphere.

Villa in Kerhonkson

Luxury Villa Escape w Private Yoga Studio

Nestled at the edge of the forest, Villa blends peaceful seclusion with refined comfort. Wake to birdsong, stretch in the private yoga studio or gather for movie night in the home theater. Large windows invite natural light and views of the trees, while indoor spaces flow naturally into the surrounding landscape. The open-concept living area is ideal for sharing meals or conversation. Whether you’r seeking stillness, inspiration, or connection, this space welcomes all with care and intention

4.95 out of 5 average rating, 229 reviews

A collage showcasing a spacious villa. One image features a tranquil private pond surrounded by trees. Another displays a warm indoor living area with comfortable seating and a game table. Additional visuals highlight an outdoor pool, a hot tub on a deck, and a modern kitchen with a large dining table.

Villa in Long Pond

INGROUND POOL OPEN ALREADY! 4500 Sq Ft POCONOS Villa, 6 bedrooms, 3 baths, private pond, back yard, hot tub, sauna, Movie/game room. Vacation rental near Camelback Mountain & Kalahari Resort. Close to the state’s #1 ski resort, highest-rated waterpark, and dozens of year-round outdoor activities, this home truly gives you the reigns to an outdoor paradise. Ski, mountain bike, golf at Mt. Airy, before returning home to create a meal in the fully equipped kitchen for the whole group to enjoy.

4.98 out of 5 average rating, 40 reviews

The exterior of a spacious, two-story house is captured at dusk, with warm lights glowing from the windows. The surrounding lawn is expansive and well-maintained, featuring soft outdoor lighting along the pathway, enhancing the serene ambiance of the property.

Villa in Wallkill

Spiti Helios: luxury retreat w/hot tub & pool

Καλώς Ορίσατε (welcome) to the beautiful Hudson Valley surrounded by distilleries, wineries (Magnanini Winery 6 minutes away 😉), spas, nature, and whatever your heart desires. Come zen out in this luxurious gem nestled on nearly 2 acres of privacy~did we mention the hot tub? *2-3 night stays get a discounted rate *Please enter all daytime visitors and overnight guests at time of inquiry. For early / late check out options check “other details”. Now let’s kick back and enjoy the Gunks!

5 out of 5 average rating, 7 reviews

The exterior of a spacious historical manor is presented, surrounded by greenery and trees. A vibrant pink flowering tree is visible to the left, while the house features multiple balconies, large windows, and a welcoming entrance. The overall setting offers a serene natural backdrop.

Villa in Neversink

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!

4.9 out of 5 average rating, 29 reviews

A Mediterranean-style villa is set against a backdrop of lush greenery, featuring a central fountain surrounded by well-maintained landscaping. The two-story structure showcases arched entryways and large windows, reflecting a harmonious blend with the natural surroundings.

Villa in Monroe

Mediterranean Villa

Whether you’re looking for a relaxing getaway or a family trip filled with adventure, you’ll love staying at the ‘Mediterranean Villa’ in the scenic Hudson Valley. Tucked away in Monroe, NY this Villa offers 5-bedrooms, 4-bathrooms, a wood-burning fireplace & enough space for your family to come together and make new memories. Location provides easy access to local attractions: take a day trip to the Catskills, shop locally at the Woodbury Commons or check out the local wineries.