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Vacation rentals in Windham

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Quick stats about vacation rentals in Windham

  • Total vacation rentals

    Explore 170 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at €77 per night before taxes and fees

  • Verified guest reviews

    Over 6,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Windham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Windham rentals

  • 4.9 Average rating

    Windham stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Windham

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

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Top guest favorite
An open floor plan living area features vaulted wooden ceilings and large windows offering views of the outdoors. Comfortable seating areas include a tan couch, black chairs, and a decorative coffee table. A dining space with a large table and an island kitchen is also visible.
Chalet in Windham

Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

4.97 out of 5 average rating, 182 reviews
Top guest favorite
A vibrant mural decorates the exterior of a barn, featuring a friendly cow alongside colorful flowers including lavender and daisies. The barn's weathered wood and metal roof provide a rustic backdrop, while the sunlight enhances the lively hues of the artwork.
Farm stay in Windham

"THE PAINTED COW" 5 acre farm in the mountains!!

"Come to nature" ALL FOUR SEASONS at our lovely renovated 1900s farmhouse set on 5 acres one mile from Windham Mountain Club. This vacation rental is perfectly suited for multi-family and friend getaways. Highlights: original artwork throughout, large country kitchen, cozy open bunk cove for kids, laptop workspaces. Outside: Starry skies, walking distance to Main St, wraparound porch, cozy evenings around the fire pit. Let the dogs and kids just run or cruise the Toboggan Hill on a snowy day.

4.99 out of 5 average rating, 110 reviews
Top guest favorite
The living room features a modern design with tall windows allowing natural light to fill the space. A black fireplace serves as a focal point, surrounded by comfortable seating. A cozy area rug enhances the atmosphere, while decor items add subtle artistic touches.
Cabin in Windham

Catskills Designer Retreat near Hiking + Swimming

★ One of Airbnb’s Most-Loved Design Homes in the Catskills ★ Relax & recharge at Casa Magda—a design-forward retreat on 9 acres in Windham, just 2.5 hours from NYC. Perfect for design lovers and nature seekers, this renovated 1980s gem blends modern style w/peaceful seclusion. Unwind in the hot tub, cozy up by the fireplace w/a record, or gather around the firepit beneath star-filled skies. Explore nearby restaurants and trails, ski Windham Mountain 7 mins away or head to Hunter in 15 mins.

4.97 out of 5 average rating, 140 reviews
Top guest favorite
Home in East Jewett

Europe in The Catskills

Welcome to "Europe in The Catskills", where your senses will commune with stunning nature and intimate surroundings, and where you will create enduring memories your family will cherish. Our European design is characterized by functionality, minimalism, and timelessness. With a neutral color palette, natural materials, functionality over form, and classic silhouettes, "Europe in The Catskills" beckons a culture of a morning espresso, an afternoon glass of Rosé, and embracing life with passion.

4.91 out of 5 average rating, 43 reviews
Guest favorite
An above ground pool is situated in a spacious yard surrounded by lush greenery. The pool's clear blue water reflects the sky, while a nearby patio area is equipped with seating and umbrellas. A charming red house serves as a backdrop, completing the serene outdoor scene.
Home in Windham

Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate offering refined luxury and comfort. Nestled within the exclusive Dingley Dell Estate, it's just a six-minute drive to Windham town and about 25 minutes from Hunter Ski Resort. The property features expansive, beautifully landscaped grounds, inviting outdoor seating areas, a prime location, and exceptional privacy. Completely renovated for ultimate guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain views.

4.95 out of 5 average rating, 108 reviews
Guest favorite
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

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.

4.95 out of 5 average rating, 511 reviews
Guest favorite
A modern kitchen is highlighted by a large island with a quartz countertop and seating. Natural light fills the space through broad windows, offering views of the surrounding greenery. Professional-grade appliances are provided, creating an inviting area for culinary activities.
Vacation home in Windham

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

4.9 out of 5 average rating, 124 reviews
Top guest favorite
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
Guest favorite
The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.
Guesthouse in Windham

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

4.98 out of 5 average rating, 198 reviews
Top guest favorite
Home in East Jewett

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.

4.99 out of 5 average rating, 151 reviews
Top guest favorite
Home in Windham

Modern Forest Retreat with Hot Tub and Sauna

This spacious, serene and secluded chalet is a newly renovated four bedroom three bathroom luxury property - 7 minutes from Windham and 15 minutes from Hunter ski resorts. Take a peaceful walk in our 6 acre forest, read by a roaring fire, relax in the spa bath, or prepare a gourmet meal in the chef’s kitchen with double oven, wet bar and coffee station. Roast marshmallows at the fire pit as you star gaze and a nightcap in the hot tub will melt all your worries away!

5.0 out of 5 average rating, 16 reviews
Top guest favorite
A spacious living area contains a light grey sofa with decorative pillows and a wooden coffee table on a patterned rug. Large windows allow natural light to filter in, highlighting a green potted plant. A red wood stove is visible on the side.
Cottage in Windham

Cozy Cottage Retreat Close to Main St/Windham Mtn

Welcome to Maplewood Cottage! Wake up to the beautiful sunshine and sounds of nature surrounded by several acres in beautiful upstate New York. It's the perfect place to relax and call home after spending a day hiking the many nearby trails of the Great Northern Catskills or shredding the slopes at Windham Mountain (4 min) or Hunter Mountain (17 min). Easily walk to Main Street (8 min) and grab some good eats at the many amazing options that Windham has to offer!

4.99 out of 5 average rating, 69 reviews

Popular amenities for Windham vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Windham's top sights

Windham Mountain

784 locals recommend

Windham Theatre

64 locals recommend

Briars & Brambles Books

37 locals recommend

Other great vacation rentals in Windham

Luxe
The spacious living area features high, vaulted ceilings with natural wood beams and an elegant antler chandelier. Large windows allow abundant natural light, offering views of the surrounding greenery. A central coffee table is complemented by a cozy sofa and several armchairs, creating an inviting atmosphere.
Cabin in Windham

NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym

5.0 out of 5 average rating, 44 reviews
Top guest favorite
A spacious kitchen features modern blue cabinetry and light countertops, complemented by natural light from large windows. An island with seating offers additional workspace, and hanging cookware is neatly arranged above, providing a practical yet stylish cooking environment.
Home in Windham

Cozy Modern: Views, 3 min ski, fire pit, game room

4.97 out of 5 average rating, 39 reviews
Top guest favorite
A spacious living area features high wooden ceilings and large windows that provide abundant natural light. A comfortable sofa and armchairs are arranged around a central coffee table, while a television is mounted on a wooden wall. A dining area with a table for six is visible in the background.
Home in Windham

Modern Ski House Minutes From The Slopes

4.94 out of 5 average rating, 94 reviews
Guest favorite
Cabin in Windham

Cozy Family-Friendly A-Frame - Windham with AC

4.95 out of 5 average rating, 20 reviews
Top guest favorite
Chalet in Jewett

Luxe Party Retreat: Ski| Pool |Karaoke|Game| Movie

5.0 out of 5 average rating, 92 reviews
Guest favorite
An A-frame cabin is nestled among snow-covered trees, showcasing large glass windows that reflect the sunset sky. The deck extends outward, surrounded by a natural landscape of snow and evergreens, creating a serene and inviting atmosphere.
Cabin in Windham

The Windham A

4.95 out of 5 average rating, 39 reviews
Top guest favorite
Home in Windham

Serenity Peaks 5BR Ranch Game Room & Mountain View

4.96 out of 5 average rating, 23 reviews
Top guest favorite
An open living and dining area features high vaulted ceilings and large arched windows, allowing natural light to fill the space. A long dining table with upholstered chairs sits centrally, while a comfortable seating area with a sofa is visible in the background.
Home in Windham

EAT, DRINK, PLAY ... and Relax in Windham

4.95 out of 5 average rating, 62 reviews

When is the best time to visit Windham?

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Frequently Asked Questions

  • What are the best places to stay in Windham?

    Many travelers choose accommodations near Main Street or by Windham Mountain for walkable access to restaurants, trails, and seasonal activities. Vacation rentals, cabins, and historic inns are frequently suggested for a variety of group sizes.

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

    Families often enjoy the Windham Path, kid-friendly activities at Windham Mountain Adventure Park, and interactive workshops at local art centers. Community events and small farms also create opportunities for hands-on learning.

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

    Explore skiing or biking at Windham Mountain, enjoy walking Main Street’s shops and galleries, and unwind in local parks. Seasonal festivals and outdoor adventure activities are central to the area’s rhythm.

  • How is the weather in Windham?

    Windham has cold, snowy winters around 16–38°F (-9–3°C) and mild summers near 62–84°F (17–29°C), with rain scattered throughout the year. Layered clothing and waterproof gear help adjust to quick weather changes in the mountains.

  • When is the best time to visit Windham?

    Late spring through early fall is often recommended for mild temperatures and outdoor festivals, while winter draws those interested in skiing and snow activities. Each season highlights a different side of Windham's landscape and community events.

  • What are the best places to visit in Windham?

    Explore Windham Mountain for skiing or mountain biking, stroll the picturesque Main Street shops, or wander local galleries. Nature parks around Windham showcase scenic trails and peaceful views.

  • What are some hiking trails in Windham?

    Try the Windham Path for a gentle, scenic walk, or the Windham High Peak Trail for more elevation and wide-ranging views. Nearby preserves feature routes through mixed forests and lively streams.

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

    Families can explore easy trails at Windham Path, enjoy outdoor adventures at Windham Mountain Adventure Park, or visit local farms for hands-on experiences. Main Street provides ice cream shops and cozy cafes for relaxed outings.

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

    Explore nearby state parks with waterfalls, wander through small Catskill towns known for arts and antiques, or visit historic sites that share the region’s story. Outdoor enthusiasts frequently suggest hiking, swimming, or seasonal festivals in the surrounding countryside.

  • Are there any pet friendly accommodations available in Windham?

    Windham has a range of pet-friendly accommodations, including cabins, lodges, and vacation rentals. You can explore options that welcome pets, making it easier to enjoy the area's outdoor spaces together.

  • What are some local tips for visiting Windham?

    Locals often suggest checking trail conditions before heading out, layering clothes for sudden weather changes, and visiting independent shops for regional treats. Early evenings are a popular time for gathering at local cafes or enjoying live music.

  • What is Windham known for?

    Windham is known for its mountain scenery, winter sports scene, and lively arts community. The town has a welcoming Main Street, access to hiking trails, and hosts community festivals throughout the year.

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

    Windham has quieter nature preserves, small art galleries, and locally owned shops that reveal a distinct character. Exploring forest trails or visiting a community farmers market gives a glimpse into local traditions.

  • What are the best foods to try in Windham?

    Windham has restaurants with locally sourced meats, New York-style pizza, and American comfort foods. Seasonal produce, baked goods, and offerings from regional breweries or cideries often feature on menus.

  • What should I bring for a trip to Windham?

    Pack layers for varied mountain weather, especially between seasons; waterproof outerwear is often useful. In winter, bring insulated clothing for 16–38°F (-9–3°C) temperatures, and consider sturdy footwear for trail exploration year-round.

  • What is the nightlife in Windham like?

    Nightlife in Windham consists of casual bars, taverns with live music, and local restaurants with relaxed atmospheres. Seasonal events sometimes feature evening entertainment or open-air concerts.

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

    Windham hosts festivals with live music, craft vendors, and celebrated food traditions, often around holidays and during summer or fall weekends. Annual events at Windham Mountain, such as mountain biking and winter sports competitions, are also frequently suggested.

  • Are there family friendly vacation rentals in Windham?

    Windham has a variety of family-friendly vacation rentals, including multi-bedroom homes, cabins, and apartments with kitchen and outdoor space. Many are located near parks and recreation areas for convenient access to activities.

Destinations to explore