Holiday houses in Windham

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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
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
4.98 out of 5 average rating, 168 reviews

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

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!

Top Guest favourite
A bright living area features large windows that provide a view of the snowy outdoors. Wooden walls and ceilings create a natural ambiance. A cozy seating arrangement is positioned around a coffee table, with additional seating options visible. A dining table is seen in the background.
Cabin in East Jewett
4.93 out of 5 average rating, 132 reviews

The Garden House - Private, Secluded, & Mt Views!

The Garden House is a cedar cabin on a mountaintop in the Great Northern Catskills. Our house is setback by a long path, on a wooded lot, and very private. It’s a place to slow down, to recharge the mind & body, and indulge in the immense beauty of the mountains. It’s cozy, made for late night cocktails by a real wood burning fireplace, and for slow mornings at the kitchen table. Our area is all-seasons with skiing, hiking, waterfalls, dipping in lakes & rivers, and plenty of fresh mountain air.

Guest favourite
A cozy bedroom features a spacious bed with a patterned quilt. Bright natural light fills the room through large windows, complemented by soft window treatments. A comfortable chair, wooden dresser, and wall-mounted television add to the inviting space's functionality and warmth.
Townhouse in Windham
4.88 out of 5 average rating, 160 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Top Guest favourite
Condo in Windham
4.9 out of 5 average rating, 230 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Top Guest favourite
A charming red chalet is nestled amidst tall evergreen trees, surrounded by a blanket of snow. The serene landscape features softly falling snowflakes and distant mountain views, creating a peaceful winter atmosphere.
Cabin in Windham
4.95 out of 5 average rating, 484 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.

Superhost
A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.
Condo in Windham
4.67 out of 5 average rating, 123 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Top Guest favourite
A cozy living space features a gray sectional sofa adorned with textured pillows and a soft throw. A rustic wooden coffee table sits within reach, complemented by a gas fireplace framed in warm wood. Natural light floods the area through a skylight, enhancing the inviting ambiance.
Guesthouse in Windham
4.99 out of 5 average rating, 186 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.

Superhost
An outdoor seating area is presented alongside a hot tub and a fire pit. The seating features a sectional sofa with light-colored cushions. Dividing panels with a leaf design create a sense of privacy, while surrounding trees provide a natural backdrop.
Cabin in Prattsville
4.87 out of 5 average rating, 295 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Top Guest favourite
A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.
Home in East Jewett
4.98 out of 5 average rating, 106 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
The exterior view showcases two townhouse units set against a backdrop of rolling hills and clear blue skies. A sprawling lawn, dotted with trees, provides open green space. Features include a stone pathway leading to the units and a fire pit area visible in the distance.
Townhouse in Windham
4.9 out of 5 average rating, 132 reviews

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.

Top Guest favourite
An outdoor deck area features a hot tub surrounded by a wooden railing. Two comfortable chairs and a wooden table provide a relaxing spot to enjoy the scenery. Large windows reflect a serene natural setting, enhancing the peaceful atmosphere of the cabin.
Cabin in Windham
4.98 out of 5 average rating, 165 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

Guest favourite
Guest suite in Windham
4.93 out of 5 average rating, 121 reviews

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter! A short walk or drive from the charming town of Windham, you're perfectly located for a country getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.

Popular amenities for Windham holiday rentals

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$703 AUD$732 AUD$562 AUD$422 AUD$427 AUD$455 AUD$481 AUD$505 AUD$444 AUD$492 AUD$492 AUD$656 AUD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Windham?

    Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in condo rentals in Windham?

    Experience the best of Windham with our condo rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there Windham house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Windham, available on Airbnb. Make a splash and soak up the sun in style!

  • Do cabin rentals in Windham have self check-in?

    Absolutely! We offer over 10 cabin rentals with self check-in in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Windham have wifi?

    Absolutely! We offer over 30 townhouse rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Windham have a bbq area?

    Absolutely! We offer over 10 cabin rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Windham?

    Windham has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Windham?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Windham

  • Total holiday rentals

    Explore 180 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $126 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 60 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!

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