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Holiday rentals in Hensonville

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Top-rated holiday rentals in Hensonville

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

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Guest favourite
Home in Durham
4.95 out of 5 average rating, 145 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Guest favourite
An outdoor fire pit sits at the center of a gravel circle surrounded by several Adirondack chairs. The chalet, elevated on a wooden deck, features a welcoming front porch and an American flag. Lush greenery and trees provide a natural backdrop.
Chalet in Hensonville
4.95 out of 5 average rating, 109 reviews

Windham Immaculate Ski Chalet Secluded Fire Pit

Super immaculate, upscale, classic ski chalet nestled on 1 private wooded acre. Close to Windham Mountain, & a short scenic drive to Hunter mountain. Features 3 bedrooms & 2 full baths & comfortably sleeps 4 adults and 4 children. Den & 2 bedrooms downstairs, complete with down comforters. 1 bedroom with a queen size bed, 1 with 2 bunk beds, sleeps 4, & full bath downstairs. Master bedroom upstairs. It has cathedral ceilings, large windows, fireplace mountain views in fall & winter. NO PETS!

Top guest favourite
A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.
Home in Cornwallville
4.98 out of 5 average rating, 184 reviews

Private Waterfall Retreat on 10 acres

Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

Superhost
A warm living area is featured, showcasing wooden walls and a vaulted ceiling. Comfortable seating is arranged around a coffee table with an assortment of plants. Large windows reveal a snowy landscape, while shelves display books and decorative items.
Cabin in Maplecrest
4.93 out of 5 average rating, 276 reviews

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Top guest favourite
A yellow cabin with a welcoming porch is pictured, surrounded by tall green grass and trees. Two wooden chairs are positioned in front, providing a serene spot for outdoor relaxation. Large windows allow natural light to enter, enhancing the cabin's inviting exterior.
Cabin in Maplecrest
4.94 out of 5 average rating, 215 reviews

Fraxinus House - Ideal for Windham & Hunter

Scenic country cabin located between Hunter Mountain and Windham Mountain, in the charming hamlet of Maplecrest. Surrounded by trees and the wilderness, it creates an idyllic mountainside escape, private and secluded grounds with only night stars and the sounds of wildlife. The decor is a mix of modern, color, and comfort, with lots of natural wood details. Both ski mountains are only a short 10 mins drive away. This is a great place for a romantic getaway or an outdoor trip in the Catskills.

Top guest favourite
A cozy living area is furnished with a plush sofa and an armchair, complemented by a round coffee table. Large windows offer expansive mountain views, while soft lighting from a chandelier creates a warm ambiance. A bookshelf with decorative items enhances the inviting space.
Townhouse in Windham
4.98 out of 5 average rating, 49 reviews

Mountain View Condo • Windham

This cozy-chic condo is our love letter to Windham. We re-built this space with heart, laughter, and far too many trips to the hardware store. Every detail has been crafted with care—we hope it brings you as much joy as it brings us. With 2 bedrooms, a queen pull-out, stunning mountain views, and everything you need for a comfortable stay, its the perfect home base in the Great Northern Catskills. Just 5mins to Windham and 10mins to Hunter—come to relax, explore, and make your own memories.

Top guest favourite
An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.
Cabin in Windham
4.95 out of 5 average rating, 504 reviews

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

Guest favourite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter
4.96 out of 5 average rating, 217 reviews

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Superhost
An open living area showcases a wooden ceiling with beams and a rustic dining table surrounded by black chairs. A cozy couch faces a brick fireplace, while a modern kitchen with stainless steel appliances is visible in the background. Soft lighting from a chandelier adds warmth to the space.
Home in Windham
4.79 out of 5 average rating, 131 reviews

Mountain Chalet Retreat New Hot Tub

Cozy Chalet style house nestled in a quiet spot and 5 minutes to Windham Mountain and close to hiking trails 15 minutes to Hunter Mountain 40 minutes to Belleayre Mountain. Relax by the fireplace after skiing TV with Netflix, Amazon and Hulu. Confortable couch with a equipped kitchen With 3 bedrooms. This property has a beautiful yard. Fairly private yet close to everything. Supermarket and restaurants near by (5 min by car) 15 min. to Colgate Lake 25 min. to Kaaterskill Falls

Guest favourite
Home in Hensonville
5 out of 5 average rating, 12 reviews

Spacious Townhome for an Upstate getaway!

Escape to this bright and comfortable townhome nestled in the heart of the Catskills. Newly built with a cozy set up, this 2-bedroom, 2-bath unit gives you the perfect mix of comfort and convenience. You’re only a few minutes from Windham Mountain, 15 minutes from Hunter Mountain and surrounded by incredible restaurants, cozy spots for a drink, and plenty of local wineries and breweries to explore. Settle in, spread out, and enjoy everything this mountain town has to offer.

Top guest favourite
Home in East Jewett
4.99 out of 5 average rating, 139 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 168 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Popular amenities for Hensonville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hensonville

Top guest favourite
A modern living space is highlighted by large windows allowing ample natural light. A cozy sofa is positioned next to a round dining table, with colorful accents and greenery present. Exposed wooden beams add warmth to the open layout, creating a welcoming atmosphere.
Cabin in Hunter
4.97 out of 5 average rating, 98 reviews

Moritz -Modern Cabin, Stunning Hunter Mtn Views

Guest favourite
Home in East Jewett
4.89 out of 5 average rating, 36 reviews

Europe in The Catskills

Guest favourite
A modern living room is highlighted by a comfortable sectional sofa and a spacious area rug. A wooden coffee table sits in the center, with a wall-mounted flatscreen TV directly across. Large windows provide natural light and views of the outside, complemented by simple decor.
Townhouse in Hensonville
4.93 out of 5 average rating, 45 reviews

Cozy townhome just minutes from Windham & Hunter

Top guest favourite
A spacious living area features a large green sectional sofa, complemented by decorative cushions. A flat-screen TV is mounted above a stone fireplace. Large windows provide natural light and views of the surrounding forest, while a coffee table is positioned in front of the seating arrangement.
Cabin in Cairo
5 out of 5 average rating, 96 reviews

The Catskill Equestrian Cabin

Top guest favourite
A living area features a stone fireplace as a focal point, complemented by a large wall-mounted television. A comfortable brown leather couch is positioned nearby, along with a rustic wooden coffee table. Warm wood flooring adds to the cozy ambiance.
Home in Hensonville
5 out of 5 average rating, 33 reviews

Windham- beautifully renovated 4BR home

Guest favourite
A comfortable living area is presented with a light-colored couch and armchair. A wooden coffee table is situated in front of the seating. A television is mounted on the wall, while natural light enters through the front door and window, enhancing the warm ambiance.
Apartment in Hensonville
4.86 out of 5 average rating, 91 reviews

Cozy condo in Windham - Near Everything!

Guest favourite
A sectional sofa in a living area is complemented by a rustic wooden coffee table. The space is brightened by natural light coming through a sliding glass door that leads to an outdoor deck. A patterned area rug adds warmth to the hardwood floor.
Home in Hensonville
4.92 out of 5 average rating, 13 reviews

Whispering River/EV/Mins to Windham and Hunter Mtn

Top guest favourite
A modern kitchen features dark wooden cabinetry and stainless steel appliances, including a microwave and oven. A decorative tile backsplash reflects light, while the countertop offers ample workspace. Soft rugs add a warm touch to the wood grain floor, enhancing the functional layout.
Townhouse in Windham
4.99 out of 5 average rating, 69 reviews

First Floor Condo with full kitchen.

Frequently Asked Questions

  • What are the best places to stay in Hensonville?

    Hensonville has a range of cozy cabins, renovated cottages, and vacation rentals near natural surroundings. Many guests choose stays close to hiking paths or within walking distance of local dining spots.

  • What are the best things to do in Hensonville with kids?

    Hensonville has spacious parks, interactive nature trails, and options for hands-on activities that families often enjoy. Many visitors explore local creeks or plan picnics near wooded areas for outdoor fun together.

  • What are some of the best things to do in Hensonville?

    Explore the area's forested trails, visit small-town shops, or sample local breakfast spots. Outdoor activities, art spaces, and seasonal festivals often draw visitors throughout the year.

  • How is the weather in Hensonville?

    Hensonville has cold, snowy winters around 16–33°F (-9–1°C) and warm, humid summers near 62–84°F (17–29°C). Shoulder seasons bring moderate temperatures and can be wetter, so pack layers and waterproof gear.

  • When is the best time to visit Hensonville?

    Late spring through early autumn is often recommended for milder temperatures and vibrant foliage, while winter attracts those interested in snow activities. Each season brings unique local events and changing landscapes.

  • What are the best places to visit in Hensonville?

    Explore local parks, community spaces, and artisan shops in Hensonville. Wandering through the wooded surroundings or visiting nearby galleries provides a taste of the region's character.

  • What are some hiking trails in Hensonville?

    Hensonville has access to forest trails that wind through the Catskill Mountains, with routes ranging from gentle walks to steeper climbs. Local trailheads often feature scenic overlooks and spots to enjoy native flora.

  • What are some family activities we can do in Hensonville?

    Families often explore scenic hiking trails, visit area parks, and join seasonal community events in Hensonville. Exploring local forests or searching for waterfalls around the region are engaging options for a day together.

  • What are some of the best day trip ideas from Hensonville?

    Many guests enjoy exploring nearby mountain villages, scenic waterfalls, or local farms known for fresh produce and seasonal events. Area art galleries and historic hamlets with local shops are also frequently suggested.

  • Are there any pet friendly accommodations available in Hensonville?

    Several vacation rentals in Hensonville welcome pets, especially those with outdoor space or nearby trails. Look for stays that mention pet-friendly amenities and check individual house rules in advance.

  • What are some local tips for visiting Hensonville?

    Layered clothing is useful as weather shifts quickly, especially in the mountains. Locals often suggest exploring lesser-known trails and engaging with small businesses for regional goods or handmade crafts.

  • What is Hensonville known for?

    Hensonville is known for its small-town atmosphere, proximity to mountain landscapes, and outdoor recreational opportunities throughout the year. Visitors often mention its community events and scenic surroundings.

  • What are the best hidden gems to explore in Hensonville?

    Locals often suggest exploring quieter forest paths, small independent galleries, and lesser-known artisan markets. Discovering tucked-away picnic spots or seasonal farm stands around Hensonville can be rewarding.

  • What are the best foods to try in Hensonville?

    Locally rooted comfort foods such as homemade pies, farm-fresh vegetables, and traditional American diner fare are frequently suggested in Hensonville. Some area eateries also highlight seasonal produce and baked treats.

  • What should I bring for a trip to Hensonville?

    Pack layers to adjust for shifting mountain weather, sturdy footwear for trails, and rain protection year-round. Consider a reusable water bottle, and if visiting seasonally, bring winter or sun gear as needed.

  • What is the nightlife in Hensonville like?

    Hensonville has a laid-back nightlife with cozy bars, casual eateries, and occasional live music at local venues. Many visitors enjoy socializing in family-run establishments or attending community gatherings in the evening.

  • What are the most popular events or festivals in Hensonville?

    Seasonal festivals, town fairs, and harvest celebrations are frequently suggested in Hensonville, with community events often held in late summer and autumn. Outdoor concerts and craft fairs are also popular gathering points.

  • Are there family friendly vacation rentals in Hensonville?

    Many vacation rentals in Hensonville are designed with families in mind, featuring multiple bedrooms, flexible living spaces, and easy access to outdoor recreation. Look for properties with child-friendly amenities or safe yard areas.

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