Airbnb your place

Holiday houses in Windham

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Windham

  • Total holiday rentals

    Explore 170 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $153 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    160 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Windham holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.9 Average rating

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

Top-rated holiday rentals in Windham

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

1 of 1 pages1 / 1
Top Guest favourite
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
4.97 out of 5 average rating, 141 reviews

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.

FamilyValueHospitality

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
5.0 out of 5 average rating, 44 reviews

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

Immerse yourself in luxury at Timber Trail Lodge, an opulent 5-bedroom, 4 full bathroom estate nestled in Windham’s premier location. This expansive 4,000 ft² home offers the ultimate mountain escape, high-end amenities such as a modern spa, chef’s kitchen, Sonos, and an outdoor fire pit, perfect for entertaining. Adventure seekers can enjoy a private zip-line and proximity to Windham Mountain 8 minutes away. Timber Trail Lodge combines modern comfort, outdoor fun, and serene Mountain View’s

LocationFamilyWalkability

Guest favourite
Home in Windham
4.95 out of 5 average rating, 108 reviews

Windham Manor | 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.

ValueFamilyQuiet

Guest favourite
Cabin in Windham
4.96 out of 5 average rating, 23 reviews

Cozy Family-Friendly A-Frame - Windham with AC

Escape to this peaceful A -Frame mountain retreat in the Catskills. Windham is know as the “Gem of the Catskills” and was recently named as a big charm town and perfect for a weekend getaway in New York by World Atlas. Only 5 minutes from Windham Mountain with skiing and snowboarding, hiking, golfing, restaurants and shops. Relax and enjoy with the whole family and friends around the fireplace, game room, or large deck. We believe without a doubt you will love this home as much as we do!

FamilyValueCheck-in

Top Guest favourite
Chalet in Windham
4.98 out of 5 average rating, 98 reviews

Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly

Now featuring our brand-new GeoDome Lounge in Windham, NY Nestled in the heart of the Catskills, this Windham retreat is just 5 minutes away from Windham Mountain resort! Wake up to breathtaking views of Windham Mountain, with skiing, hiking, biking, and more just minutes away. After exploring, unwind in the hot tub, rejuvenate in the sauna, relax in the NEW dome lounge, walk around the 1.4-acre property, or gather around the fire pit. Our mountain escape invites unforgettable memories.

ValueFamilyDecor

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, 512 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.

ValueLocationCheckout

Top Guest favourite
The living room features a wall of large windows that offer views of surrounding mountains. A combination of leather and upholstered seating is arranged around a coffee table, with a light area rug underfoot. Wooden ceilings and natural light contribute to a spacious atmosphere.
Chalet in Windham
4.98 out of 5 average rating, 174 reviews

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern 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!

FamilyLocationSleep quality

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, 231 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!

FamilyValueKitchen

Guest favourite
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
4.98 out of 5 average rating, 198 reviews

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.

LocationFamilyComfort

Guest favourite
Condo in Windham
4.98 out of 5 average rating, 45 reviews

Slope Side Luxe | Views, Decks, Walk to Mtn & Town

This brand new 3600 sqft luxury condo, consisting of 5 bedrooms and 5 1/2 baths, is situated directly across from Windham Mountain. Private bathrooms for each bedroom. Large living space built for large groups with refined palates. Skiing and the adventure park are within walking distance. Close to mountain biking and hiking, and 1mi from golf at Windham Country Club. 1,000 sq ft of private decks to take in mountain mornings and unwind with a latte. Managed by Cedar Properties.

LocationValueAccuracy

Top Guest favourite
Cabin in Windham
4.95 out of 5 average rating, 226 reviews

Cozy Creekside Cabin | 5 Mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

FamilyLocationQuiet

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
5.0 out of 5 average rating, 103 reviews

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!

FamilyLocationNearby

Popular amenities for Windham holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Windham's top sights

Windham Mountain

784 locals recommend

Windham Theatre

64 locals recommend

Briars & Brambles Books

37 locals recommend

Other great holiday rentals in Windham

Top Guest favourite
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
4.97 out of 5 average rating, 39 reviews

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

FamilyLocationWalkability

Top Guest favourite
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
4.95 out of 5 average rating, 62 reviews

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

LocationFamilyComfort

Top Guest favourite
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
4.99 out of 5 average rating, 70 reviews

Cozy Cottage Retreat Close to Main St/Windham Mtn

ValueLocationLayout

Top Guest favourite
Home in Windham
5.0 out of 5 average rating, 16 reviews

Modern Forest Retreat with Hot Tub and Sauna

LocationFamilyHot tub

Guest favourite
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
4.95 out of 5 average rating, 40 reviews

The Windham A

FamilyLocationCheck-in

Top Guest favourite
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
4.94 out of 5 average rating, 94 reviews

Modern Ski House Minutes From The Slopes

LocationValueQuiet

Top Guest favourite
A modern kitchen is showcased with a large island featuring ample seating for six. Stainless steel appliances, including a refrigerator and a microwave, complement white cabinetry. Natural light enters through windows above the sink, highlighting the open space and wooden ceiling beam.
Home in Windham
4.98 out of 5 average rating, 57 reviews

Beautifully restored 6 BR in the heart of Windham

LocationFamilyBarbecue

Top Guest favourite
The spacious living area is featured, showcasing large windows that frame expansive mountain views. A plush sofa and wooden coffee table occupy the center, complemented by two armchairs. A side table with a decorative vase adds a touch of elegance to the room, illuminated by natural light.
Home in Windham
4.98 out of 5 average rating, 42 reviews

“Amazing Mtn & Ski Slope Views “

FamilyLocationHot tub

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$847 NZD$801 NZD$680 NZD$595 NZD$595 NZD$595 NZD$581 NZD$610 NZD$537 NZD$595 NZD$595 NZD$794 NZD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

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