Vacation rentals in Windham

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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
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill
4.97 out of 5 average rating, 193 reviews

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Guest favorite
A cabin exterior is illuminated at night, with steps leading to a doorway. A friendly dog sits on the porch, while a fire pit glows nearby. Colorful chairs are positioned around the fire, surrounded by trees, creating a cozy outdoor setting.
Tiny home in Hunter
4.91 out of 5 average rating, 130 reviews

Home Alone Tiny

Get away from it all. Enjoy peace and quiet in this 200-sq foot home in Jewett NY, 5 miles away from Hunter Mountain and 9 miles from the Windham Mountain. The house is set on an acre of woods by the quiet local road that enables an easy access. The loft is used as a bedroom with the queen size bed. The view from two large windows makes you feel like you sleep in the treehouse. If you want to spend most of the time outside, there’s a picnic area with a gas grill, a fire pit, and a large deck.

Top guest favorite
Condo in Windham
4.9 out of 5 average rating, 229 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.

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 favorite
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.

Top guest favorite
The log cabin features a sloped metal roof and large windows, surrounded by trees. A spacious wooden deck with a railing offers outdoor seating options. The area is adorned with fallen leaves, enhancing the natural setting.
Cabin in Margaretville
4.94 out of 5 average rating, 210 reviews

Catskills log cabin in the sky with mountain views

Welcome to Cabin in the Sky! At 1,671 ft elevation, Cabin in the Sky is a newly renovated log cabin nestled in the mountainside with tranquil views. The home offers the perfect combination of seclusion and convenience. In the mornings/evenings, enjoy a cup of coffee or glass of wine from the private deck which overlooks pure nature (not a car, street or building in sight). During the day, take advantage of the local hiking, skiing, farmer's markets, restaurants and shopping.

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, 294 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 favorite
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, 104 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 favorite
Guest suite in Woodstock
4.99 out of 5 average rating, 200 reviews

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Top guest favorite
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.

Superhost
A living room features a stone fireplace with a wood-burning fire, complemented by a mounted flat-screen TV above. The hardwood floor adds warmth, while artwork of trees decorates the wall. A comfortable couch invites relaxation next to a stack of firewood.
Townhouse in Windham
4.83 out of 5 average rating, 204 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Spacious 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails.

Top guest favorite
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, 163 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.

Popular amenities for Windham vacation rentals

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR8,018 ZARR8,355 ZARR6,415 ZARR4,811 ZARR4,875 ZARR5,196 ZARR5,484 ZARR5,757 ZARR5,067 ZARR5,613 ZARR5,613 ZARR7,489 ZAR
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

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 house rentals in Windham?

    Experience the best of Windham with our house rentals, starting at about $140 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 50 vacation rentals for guests traveling with pets.

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

    Absolutely! We offer over 40 house rentals with self check-in in Windham. Enjoy a tailored experience with all the comforts you desire.

  • 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 condo rentals in Windham have wifi?

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

  • Do house rentals in Windham have a bbq area?

    Absolutely! We offer over 60 house 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 condo rentals in Windham?

    Windham has more than 10 family-friendly condo 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 vacation rentals in Windham

  • Total vacation rentals

    Explore 180 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at R1,443 ZAR 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 60 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!

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