House vacation rentals in Windham

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Top-rated house rentals in Windham

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

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 640 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Nov 19 – 26

R2,513 ZAR per night

Guest favorite

Home in Prattsville

4.95 out of 5 average rating, 111 reviews

12acres Catskill Mntn vws, hot tub, fire pit, pond

Get away to this beautiful remote location in the Catskills region. Stunning views of mountains and over 12 acres of land to explore. Located on the property is also a new hot tub, fire pit & a serene pond where you can just sit back and take in the views. We are about a 15 minute drive away from Windham Mountains ski resort, 13 minutes to Bearpen Mountain Sports, less than 30 minutes to Hunter Mountain and less than 40 minutes to Kaaterskill Falls (the most famous Catskill Mountain waterfall).

Jun 25 – Jul 2

R4,560 ZAR per night

Guest favorite

Home in Roxbury

5.0 out of 5 average rating, 125 reviews

Private 3BR escape w/ sweeping Mt Views & Firepit!

Click: "Show more" to read description before booking. NO PETS Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse with mountain views. Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min from Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours!

Apr 6 – 13

R6,129 ZAR per night

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 271 reviews

Yanity House

You will have access to the entire house fully furnished. Pet's are welcome just keep paws clean its a beige rug. We want everyone to be comfortable, so please let us know how and what you would like to see improved if you rent the unit. We will improve the unit as per guest suggestions. Currently we do not have cable but we do have a dvd and game system in the living room - All the bedrooms have TV's, dvd players or bring your streaming device There currently is no phone but cell service works

Oct 10 – 17

R2,104 ZAR per night

Guest favorite

Home in Durham

4.96 out of 5 average rating, 101 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Sep 25 – Oct 2

R7,866 ZAR per night

Guest favorite

Home in Catskill

4.99 out of 5 average rating, 134 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Athens, NY Entire House - 1 bedroom Quiet Country setting Springtime - or anytime is a great time to escape to upstate NY. Guests have called it "a very cozy cottage in the woods". It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. Area features outdoor activities: hiking trails, skiing and kayaking.

Feb 9 – 16

R2,974 ZAR per night

Guest favorite

Home in Windham

4.95 out of 5 average rating, 105 reviews

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Beautiful Country setting, Large fire pit across bridge next to beautiful stream w 6 Adirondack chairs,new stream side bluestone patio.2.6 miles from Ski Windham. Modern spacious kitchen Wolf &Sub Zero , Breville Barista espresso machine, comfy living rm with pellet stove and 1906 antique player piano, flat screen smart TV. Large deck with stream view ,outdoor flat screen tv. Newly installed 6 Person Hot Tub w waterfall,2 person shower for relaxation after a hike. Gas fire table on deck also.

Mar 19 – 26

R7,395 ZAR per night

Guest favorite

Home in Windham

4.98 out of 5 average rating, 120 reviews

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

~~ One of the top rated AirBNBs in all of Windham. 4.97 with 100+ reviews ~~ The perfect ski and getaway home for groups of families, w/six large bedrooms that sleep 16+ comfortably. Nestled on 55 acres, our serene, sun-drenched home is just a few miles from the Slopes. Includes 3 full baths, an outdoor hot tub, game room, and a huge wrap around deck w/ propane grill. Create memories around our outdoor fire pit, or snuggle up at the fireplace in our spacious living/dining room.

Nov 7 – 14

R14,432 ZAR per night

Superhost

Home in Windham

4.92 out of 5 average rating, 153 reviews

Windham Mountain Getaway- soak, relax, unwind

*** Now offering late checkout*** Warm and ready for the season, this newly renovated retreat is perfectly situated in the town of Windham, New York. Whether it’s hike, bike, or ski there’s plenty to offer year round! Consisting of 4 private bedrooms, 2 bathrooms and plenty of open floor space bring the whole family and feel right at home with this beautiful modern mountain getaway. Spend time enjoying the privacy from the decks, soaking in the hot tub or relaxing in the sauna.

Jul 15 – 22

R8,307 ZAR per night

Guest favorite

Home in Prattsville

4.96 out of 5 average rating, 137 reviews

Chalet On The Far Side Of The Mountain - Catskills

We are so excited to welcome you to our expansive log home situated on 7 private acres with breathtaking views of the mountains! We are located in the heart of the Catskills and just 20 minutes away from Hunter/ Windham Mountains. An ideal four-season getaway. Enjoy hiking, skiing/snowboarding, fly fishing, and or a magical rail bike ride with magnificent views. Soak up the mountains in the hot tub or cozy up under the stars by the outdoor stone fireplace right on the deck!

Sep 6 – 13

R17,875 ZAR per night

Guest favorite

Home in Roxbury

4.96 out of 5 average rating, 103 reviews

Mountain and tree view cabin on 12 private acres

A great escape awaits you on 12 acres of private land. If you prefer a relaxing vacation or if you want to get involved in local activities (hiking, biking, swimming, skiing, snowshoeing, sledding), this is your place. Enjoy 360 degree views of the Catskill Mountains from almost anywhere on the property. Sip your morning coffee while watching the sunrise on the large deck. Play in the large private yard. Clear evenings are the best for sunsets, a fire pit and star gazing.

Oct 28 – Nov 4

R3,995 ZAR per night

Guest favorite

Home in Windham

4.93 out of 5 average rating, 166 reviews

Extreme leisure minutes from action and adventure

Relax and unwind in uniquely styled home on secluded 14-acre private property. Conveniently located to Windham mountain, vineyard, horseback riding and hiking trails The Bridge as we lovingly call our home, was designed to be a space where extreme leisure is met with adventure. Wake up early enough, you will see deer and wild turkey graze through the meadow. Stay awake late enough and gaze upon the endless stars. Now with hi-speed wifi!! Follow us @TheBridge_windhamNY

Apr 15 – 22

R8,755 ZAR per night