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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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Top guest favourite
A serene landscape is presented with rolling green hills under a clear blue sky. The glowing sun rises on the horizon, illuminating the dewy grass and trees. Fenced areas and distant hills contribute to the peaceful atmosphere of the mountain top.
Farm stay in Conesville

6 Bedroom 1860 Farmhouse Mountain Views Windham

Near Windham! Take time away from it all to enjoy a beautifully situated private farm on a 150- acre mountain top. Favorite things to experience are exploring the wilderness, waterfalls, farm animals, the sunrise from the front porch, the sunset view from the upper mountain field, collecting eggs, skiing, snowshoeing, cross country skiing, sledding, Lake access at Huyck Preserve (kayak, swimming hiking, picnics), cooking farm fresh meals (farm to table ingredients by the season). Exquisite stars

4.99 out of 5 average rating, 107 reviews
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

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!

4.96 out of 5 average rating, 115 reviews
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

Cozy townhome just minutes from Windham & Hunter

Welcome to the Catskill Cozy at Windham! At just over 1,250 square feet and boasting 2 bedrooms, 2 bathrooms, and a full kitchen, this private townhouse is sure to provide all of the comforts of home. Plus, this cozy getaway is located just 4 minutes from Windham Mountain and 12 minutes from Hunter Mountain. Can you say “quick access to the slopes?” Hi-speed WiFi for anyone looking to work, and a super comfortable living room equipped with blankets and comfy couches for those looking to relax.

4.94 out of 5 average rating, 51 reviews
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

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.

4.94 out of 5 average rating, 220 reviews
Top guest favourite
Home in Jewett

Lux Hunter Mountain Retreat | Sauna + Game Room

NEW ♨️ Private Sauna + Family Game Room! Escape to our beautifully remodeled 3BR/2BA mountain retreat set on 6 private acres in Jewett. Relax in your private indoor sauna or enjoy the game room with arcade, foosball, and darts. 📍 ~10 minutes to Hunter & Windham Mountains 📍 ~2.5 hours from NYC — an easy year-round getaway Ski, hike, bike, swim, golf, fish, explore local vineyards, or dine out — all within 10 minutes. Then return to comfort, space, and peaceful mountain surroundings.

4.96 out of 5 average rating, 103 reviews
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

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!

4.96 out of 5 average rating, 230 reviews
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

Windham- beautifully renovated 4BR home

Enjoy our newly renovated home located less than 5 minutes from Windham Mountain. Situated in the heart of the Windham area, Blue Birch House has just finished a complete renovation, and has everything you need for an amazing mountain vacation. This welcoming home features 4 bedrooms and can accommodate up to 8 guests. It also features 2 full baths, a fireplace, dining room, new kitchen, full laundry, front and back porches. Walk to dining, 5 minutes to hiking, WIndham, and lake.

5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Hensonville

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-king 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.

5.0 out of 5 average rating, 13 reviews
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

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.

4.99 out of 5 average rating, 180 reviews
Superhost
A stylish living area showcases a mid-century modern sofa adorned with various textured cushions. Two green armchairs are positioned nearby, facing a coffee table made from natural wood. A floor lamp and a piece of mountain-themed wall art add to the cozy ambiance.
Townhouse in Hensonville

Spacious 2 Bdr. Townhome Minutes from Windham Mtn

Make this spacious, newly built townhouse yours during a relaxing getaway in the Catskill Mountains! Located just minutes from Windham Mountain, this 2 Bedroom/2 Bathroom townhouse is packed with amenities for you to enjoy your stay. Be sure to enjoy at least one of the many great restaurants just steps from the front door, spend some time at one of the breweries or wineries located less than 15 minutes away, and enjoy all that the Catskills has to offer!.

4.96 out of 5 average rating, 77 reviews
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

The Catskill Equestrian Cabin

Decompress in this beautiful, calm, serene new cabin build nestled in the mountains on a peaceful, private five acre lot, bordering an equestrian center. Walk less than two minutes to see the horses during your stay. The cabin is less than 15 minutes to Windham mountain for winter skiing and under 20 minutes to the popular town of Catskill. This cabin has all the amenities you need for a wonderful stay. We hope to host you soon!

5.0 out of 5 average rating, 102 reviews
Superhost
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

Cozy condo in Windham - Near Everything!

Welcome to our cute & cozy condo. Located between Hunter (12 min) and Wyndham Mountain (7 min). Short drive to restaurants/shops and a few walking distance options. This 2 bedroom, 1.5 baths one-level condo is packed with amenities for you to enjoy your stay. Fully equipped kitchen in case you decide to stay in. Several ac units. Enjoy our comfy beds, open concept, board games, easy street parking…. And great hosts :)

4.83 out of 5 average rating, 98 reviews

Popular amenities for Hensonville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hensonville

Guest favourite
An outdoor deck is displayed, featuring a comfortable seating arrangement with gray cushions on a rug. A round hanging chair is visible, accompanied by a potted plant. The backdrop includes greenery, enhancing the overall setting.
Home in Hensonville

Wake Up to Mountain Magic Year-Round (Hot Tub)

4.97 out of 5 average rating, 86 reviews
Guest favourite
A serene view of a two-story chalet surrounded by greenery, featuring a spacious fire pit area with several Adirondack chairs. Large trees provide shade while a wooden deck with seating overlooks the yard. The warm sunlight highlights the brick and wood exterior of the house.
Chalet in Hensonville

Serene two-level Chalet, 3 minutes from Windham.

4.95 out of 5 average rating, 21 reviews
Top guest favourite
The timber frame chalet is showcased in the evening light, highlighting its expansive front porch and large windows. Surrounding greenery features an array of trees and shrubs, while a stone pathway leads to the entrance, creating an inviting aspect to the property.
Chalet in Hensonville

Hilltop Family Escape + hot tub, 4 min to slopes

4.99 out of 5 average rating, 85 reviews
Superhost
Home in Hensonville

Cozy 2BR Catskills Cabin | Windham & Hunter

5.0 out of 5 average rating, 4 reviews
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

Whispering River/EV/Mins to Windham and Hunter Mtn

4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in East Jewett

Europe in The Catskills

4.91 out of 5 average rating, 43 reviews
Guest favourite
Chalet in Hensonville

Spa Retreat 5 Min to Windham • Hot Tub • Sauna •EV

4.88 out of 5 average rating, 42 reviews
Superhost
A spacious living area features a cozy seating arrangement with a striped sofa and green armchairs. A wood-burning fireplace is centrally located, surrounded by light wood paneling. A dining table sits nearby, complemented by large windows that provide views of the outdoor greenery.
Home in Hensonville

Big Hollow! Close to The Henson/Wylder

4.89 out of 5 average rating, 87 reviews

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.

Destinations to explore