House vacation rentals in Windham

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

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 w/ sweeping 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 to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

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

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.

Private Waterfall Retreat on 10 acres

Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

Custom Catskills private retreat

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

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!

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.

Great for hunters-skiers-hikers close to Windham

The quiet tranquility of mountain nature. Minutes from the Windham mountain ski resort. State land nearby for hunters as well. This one bedroom home has key pad entry, a full kitchen, dining area, living room, front deck, spacious rear deck, fire pit, acres of back yard, full bathroom, can sleep four with queen size bed and pull out couch, wifi, fire stick tv. All the comforts of home. This is a fully furnished one bedroom home that was recently converted to an Air BNB.

b/w Hudson&Hunter, a Catskill Unit Made for Snugs

Welcome to the Catskills and rest up in this calm, small, and stylish space! We recently rebuilt the entire interior of an old brick building and imagined the first floor (*** the entrance is at the back of our house***) as a guest unit for our friends & family during visits. When we do not have friends & family visiting, we are offering this space to you! We are architects by training and have placed our aesthetic energy in making this unit modern but also cozy.

Modern Prefabricated Architectural Retreat

At Stonewall Hill, a modern prefab home set on 10 wooded acres, you can enjoy a cozy night by the fire in winter & cook a feast in the well-equipped kitchen or on the outdoor gas grill in summer. It has an open plan kitchen, living & dining space; a main bedroom w/ queen bed & ensuite bathroom; a 2nd bedroom that doubles as TV room w/ queen sofa bed & bathroom across the hall. 10 minutes to the HITS fairgrounds & close to hiking, skiing, shopping, & dining.

Gingerbread House- a 1950s Catskills Chalet

Perched high among the trees, Gingerbread is a 1950’s Swiss chalet that sits on 4 acres. This is the house everyone slows down for, points and says ‘ that’s the house I would want Upstate’. Well ….she's taken. But I am so happy to welcome you as guests for a short period of time. Gingerbread comes with all the little touches making it feel like the perfect home away for a week, weekend or however long you can escape your regular life.