Villa holiday rentals in Monticello

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Top-rated villa rentals in Monticello

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!

Top guest favourite
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
4.98 out of 5 average rating, 53 reviews

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

Superhost
Villa in Tobyhanna
4.93 out of 5 average rating, 75 reviews

Poconos Themed Villa, Heated Pool, HotTub, Theater

Journey to Villa Vincente to reconnect with each other at a private nature resort in the heart of the Poconos. Discover your own oasis in greenhouse poolroom with sunken lounge by the water. Host an event at the open chef's kitchen or Rooftop Garden for 21guests. Never leave the villa and enjoy the underground club with a theater or the hot tub under twinkling stars Bring together the entire family with 6BR and accessible first floor. Give your loved ones a place where nature did the decorating.

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.

Guest favourite
Villa in Tobyhanna
4.87 out of 5 average rating, 23 reviews

Majestic Villa at Pocono/Kalahari/HotTub/Game Rm

Stay in a modern and spacious villa in a prime location in Pocono. Our 4-bedroom, 2.5-bathroom home has been recently upgraded with style. You can easily access the best of Pocono, such as Kalahari, Camelback, lakes, and parks. Enjoy the luxury of Pocono Farm Club, with a pool, a lake, a golf course, and more. Escape the city and relax in our cozy and comfortable home. The villa is located in a community that offers a lot of amenities like a swimming pool, Golf, lake, a kid's park & restaurant.

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 Mntn Estate, Hotub, Pond, 21+ppl

Refresh 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!

A spacious sunlit living area is framed by large windows, inviting natural light and offering views of the snow-covered landscape. Vintage furniture is arranged around a central coffee table on a patterned rug, with decorative elements and a rock feature enhancing the room's unique character.
Villa in Hawley
4.75 out of 5 average rating, 20 reviews

1 Mi to Lake Wallenpaupack: Spacious Poconos Villa

Bring your family or friends to this Hawley vacation rental for a unique and memorable group getaway! Boasting vintage decor, 5,112 square feet of living space, and a deck for relaxing outdoors, this 6-bedroom, 3.5-bath villa provides an ideal place to spend quality time with your loved ones. Venture out and you can easily enjoy aquatic activities on Lake Wallenpaupack or visit Poconos hotspots like ski resorts and water parks. Afterward, relax with an idyllic backdrop of the indoor koi pond!

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
4.86 out of 5 average rating, 104 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!

Guest favourite
A spacious outdoor area features a large swimming pool surrounded by a paved patio. The villa, with a red-tiled roof, stands in the background amidst lush greenery. Sun loungers are arranged at the pool's edge, inviting relaxation.
Villa in Monroe
4.95 out of 5 average rating, 58 reviews

Mediterranean villa •pool•hot tub•fire place

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, outdoor fire pit ,Smart TVs, a private hot tub, spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and Legoland. Unwind, explore, and indulge in upscale relaxation year-round.

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 favourite
A tranquil outdoor space features a stone fire pit surrounded by a manicured lawn. A single blue adirondack chair is positioned nearby, offering a peaceful spot to relax while enjoying the views of the surrounding trees and open meadow.
Villa in New Paltz
4.91 out of 5 average rating, 23 reviews

Beautiful 5BR Hudson Valley Villa

RELAX AND PLAY in beautiful updated sun-drenched 5 BR/3 BA home with Great Room, modern kitchen, yoga sunroom, and spa-like primary BA w 6-foot soaking tub. Amazing outdoor space w giant pool, patio, firepit, grill. Max occupancy is 10 people. No Pets. A modern oasis in the Hudson Valley near hiking, rock-climbing, road and gravel cycling, skiing, apple-picking, antiquing, bird-watching and other fun seasonal activities.

Top guest favourite
Villa in Kerhonkson
4.97 out of 5 average rating, 326 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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