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Holiday houses in Windham

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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 $128 AUD 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 grill 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.

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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, 139 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.

LocationFamilyHot tub

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, 54 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.

LocationFamilyNearby

Guest favourite
Cabin in Windham
4.95 out of 5 average rating, 20 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!

FamilyLocationIndoor spaces

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, 507 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.

FamilyValueWalkability

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, 37 reviews

The Windham A

Discover year-round comfort and style at this beautifully designed A-frame cabin just 5 minutes from Windham Mountain and 20 minutes from Hunter Mountain. With 3Beds, 3Baths, and a loft, this modern retreat is perfect for families, couples, or friends seeking a peaceful escape in the Catskills. Step downstairs to a fully finished basement that features a game room, private theater room, and a stylish bar area—perfect for après-ski gatherings, movie nights, or fun with friends and family.

LocationFamilyTV

Top 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, 222 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!

FamilyValueHiking

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, 72 reviews

First Floor Condo with full kitchen.

Relax in this beautifully appointed studio Condo in Windham NY just 2 miles from the base at Ski Windham. Windham provides a wealth of year-round activities. The surrounding area is ideal for hiking, skiing, golfing, biking, fishing, snowmobiling and horseback riding. Scenic views abound. Come enjoy Windham's fine dining establishments, full service spas, world class ski resort, two golf courses, breweries, wine bars, unique shops, movie theater and fine art galleries.

ValueFamilyIndoor spaces

Top Guest favourite
Cabin in Windham
4.95 out of 5 average rating, 220 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.

FamilyLocationCleanliness

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, 174 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.

ValueLocationPool

Guest favourite
Home in Windham
5.0 out of 5 average rating, 13 reviews

The Mad Brook House | Walk to Main St, Windham

Walk to Main Street from this cozy Catskills cottage by the brook! The Mad Brook House is a newly refreshed two-bedroom, one-bath retreat in the heart of Windham — perfect for couples, small families, or friends visiting the mountains. Dating back to 1940, the home has been beautifully updated to combine classic Catskills character with modern comfort. Relax beside the gentle brook just steps from your door, or stroll to Main Street for dining, shopping, and coffee!

LocationFamilyNearby

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

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!

LocationFamilyComfort

Top Guest favourite
The cozy cabin exterior is lit softly by string lights as dusk sets in. A fire pit surrounded by adirondack chairs occupies the grassy area in front, while large windows offer glimpses of the warm interior and the surrounding forest.
Cabin in Prattsville
4.99 out of 5 average rating, 204 reviews

Alpine Ridge - Mtn. Views, Fire Pit, Pizza Oven

Alpine Ridge sits on 3 private acres at the top of a quiet mountain road, with sweeping views of the Bearpen Mountain Range across the valley. Thoughtfully designed and curated, our home is a peaceful escape that still keeps you close to essentials—5 minutes to Prattsville, 15 minutes to Windham, and 25 minutes to Hunter. The Catskills offer endless hiking, skiing, charming towns, local events, wedding venues, and farm-to-table dining. Follow us: @alpineridgeny

ValueFamilyHeating

Popular amenities for Windham holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Windham's top sights

Windham Mountain

780 locals recommend

Windham Theatre

64 locals recommend

Briars & Brambles Books

37 locals recommend

Other great holiday 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
5.0 out of 5 average rating, 42 reviews

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

LocationFamilyAccuracy

Guest favourite
Condo in Windham
4.98 out of 5 average rating, 44 reviews

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

FamilyLocationSkiing

Guest favourite
A cozy firepit area is surrounded by four adirondack chairs, set on a bed of gravel. The inviting glow of the fire contrasts with the serene backdrop of trees. The log cabin is visible in the background, with warm light emanating from its windows.
Cabin in Jewett
4.87 out of 5 average rating, 39 reviews

The Woodland Getaway, close to Hunter & Windham!

ValueLocationLayout

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
5.0 out of 5 average rating, 66 reviews

Cozy Cottage Retreat Close to Main St/Windham Mtn

ValueLocationHeating

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, 37 reviews

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

LocationFamilyKitchen

Top Guest favourite
Home in Catskill
5.0 out of 5 average rating, 12 reviews

Cozy stylish Cabin in the Woods

LocationAccuracyCheck-in

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, 99 reviews

The Catskill Equestrian Cabin

FamilyLocationNearby

Guest favourite
Home in Windham
5.0 out of 5 average rating, 21 reviews

Peaceful Woods at The Johnson Cottage

LocationFamilyAmenities

When is the best time to visit Windham?

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Avg. price$706 AUD$667 AUD$567 AUD$496 AUD$496 AUD$496 AUD$485 AUD$509 AUD$448 AUD$496 AUD$496 AUD$662 AUD
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