House vacation rentals in Windham

A modern kitchen features dark cabinetry and an island with seating. Light streams in through large windows, illuminating a wooden dining table surrounded by black chairs. The space offers a blend of style and functionality, with appliances and countertop arrangements visible.

4.96 out of 5 average rating, 115 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 gas fireplace 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.

FamilyValueAir conditioning

4.81 out of 5 average rating, 129 reviews

Ski Hunter Mountain w/ Views | Fire Pit | 5 Acres

Escape to your 5-acre mountain retreat! This spacious 3-bed home combines modern comfort with Catskills charm—perfect for families, friend groups, and outdoor enthusiasts. ✨ 5 private acres w/ breathtaking mountain & meadow views ⛷️ 6 min to Hunter Mountain skiing & snowboarding 🏔️ 8 min to Windham Mountain 🔥 Cozy gas fireplace + outdoor fire pit 🌅 Stunning sunset views from your private meadow 📺 65" HDTV with Netflix, Hulu, Disney+, HBO 🍳 Fully equipped kitchen + BBQ 💻 High-speed WiFi

FamilyLocationView

The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.

5.0 out of 5 average rating, 421 reviews

Private cabin in the Catskills

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 :)

LocationValueSleep quality

4.95 out of 5 average rating, 109 reviews

Grand Mansion | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate blending refined luxury, comfort, and privacy. Nestled within the exclusive Dingley Dell Estate, just six minutes from Windham town and 25 minutes from Hunter Ski Resort. Enjoy beautifully landscaped grounds, inviting outdoor spaces, complete privacy, and breathtaking mountain views. Fully renovated for exceptional comfort, the home features a private pool, movie room, premium sound system, and everything needed for an unforgettable luxury mountain escape.

LocationFamilyWifi

4.96 out of 5 average rating, 105 reviews

Home in Jewett

Lux Hunter Mountain Retreat | Sauna + Game Room

NEW ♨️ Private Sauna + Family Game Room! Escape to our beautifully remodeled 3BR/2BA mountain retreat set on 6 private acres in Jewett. Relax in your private indoor sauna or enjoy the game room with arcade, foosball, and darts. 📍 ~10 minutes to Hunter & Windham Mountains 📍 ~2.5 hours from NYC — an easy year-round getaway Ski, hike, bike, swim, golf, fish, explore local vineyards, or dine out — all within 10 minutes. Then return to comfort, space, and peaceful mountain surroundings.

FamilyValueCheckout

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.

4.95 out of 5 average rating, 235 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!

FamilyLocationQuiet

Superhost

The chalet's exterior showcases a large wooden structure with a distinctive peaked roof. Expansive windows reflect sunlight, enhancing the natural surroundings. A spacious wrap-around deck is visible, surrounded by lush green grass and trees, providing a peaceful setting on the property.

4.94 out of 5 average rating, 177 reviews

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

~~ One of the top rated AirBNBs in all of Windham. 4.98 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.

ValueFamilyCondition

4.97 out of 5 average rating, 108 reviews

Home in Prattsville

Catskills Retreat - Game Room, Hot Tub, EV charger

Welcome to our Mountain Chalet. Bring the whole family to this spacious retreat with plenty of room for fun and relaxation.This specious house, nestled on 2.5 acres, features 4 bedrooms, 3 full bathrooms, Hot Spring hot tub, a game room, a cozy gas fireplace, smart TVs, an EV charger and more. It has beautiful views. Located in the heart of the Catskills, 15 min from Windham Mountain, 20-25 min from Hunter and 40 min from Belleayre. Your perfect mountain getaway awaits!

LocationFamilyNearby

4.99 out of 5 average rating, 158 reviews

Home in East Jewett

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.

LocationValueKitchen

An open-concept living area features a deep leather couch and two comfortable chairs, with large sliding glass doors offering expansive views of the autumn foliage and mountains. A round wooden coffee table complements the space, which is accented by a textured light fixture and a dining table in the background.

4.99 out of 5 average rating, 163 reviews

Lux Modern Cabin at Hunter Mountain

Modern private retreat in the heart of the Catskills with expansive views of Hunter Mountain that delivers an ultra-lux getaway experience. Casa Nevana is a brand-new construction. Enjoy each season of the Catskills in comfort and style. Immerse yourself in nature and slow living while experiencing luxurious accommodations and impeccable design. Follow us on IG @CasaNevana to see more of the home, local hot spots and more!

ValueFamilyDecor

The image displays a charming red house with two stories, featuring a welcoming front porch with white railings. A snow-covered yard surrounds the home, while a large tree is positioned to the left. The clear blue sky adds to the serene atmosphere.

4.91 out of 5 average rating, 144 reviews

Big Red Retreat 3 min to Windham Mountain & Golf!

Welcome to Big Red – Your Ultimate Mountain Retreat! Nestled in the heart of the scenic Windham area, Big Red invites you to experience the perfect blend of comfort, convenience, and adventure. Whether you're here to hit the slopes at Windham Mountain, explore the tranquil Windham Path, or tee off at the nearby golf course, our spacious 6-bedroom, 2.5-bath home is your ideal basecamp for an unforgettable getaway.

FamilyLocationSleep quality

4.93 out of 5 average rating, 109 reviews

An inviting fire pit area is surrounded by six green Adirondack chairs arranged in a circle, set on a stone path of gray gravel. In the background, a multi-level deck extends from the house, surrounded by trees in a serene outdoor setting.

Home in Hensonville

Mountain-Modern 5BR Home • Windham & Hunter • EV

A 5 bedroom , spacious, 5-acre mountain modern home boasting all comforts and amenities you could need in the heart of the Catskills! The house is tucked away, secluded, meanwhile just minutes away from lakes, hike trails, golfing, ATV rentals, breweries, farmers markets, restaurants, vineyards, local shops and skiing or snowboarding at either Windham Mountain resort or Hunter Mountain! Welcome to GreeneHaus!

LocationFamilyIndoor spaces

Popular amenities for Windham house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 102 reviews

Home in Tannersville

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge

ValueLocationOutdoor spaces

A wooden deck features a circular cedar hot tub surrounded by greenery. Two blue and white striped towels hang on a nearby fence, while a basket is positioned to the side. The scene suggests a tranquil outdoor space for relaxation and enjoyment.

4.98 out of 5 average rating, 133 reviews

Hunter Creek House w/ Hot Tub, Firepit, BBQ, Deck

LocationValueGetting around

4.96 out of 5 average rating, 185 reviews

A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.

Home in Woodstock

Woodstock Historic Artist Estate- The Museum House

LocationValueLayout

4.99 out of 5 average rating, 279 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

ValueLocationDecor

An illuminated in-ground pool reflects a calming turquoise hue under the night sky. The pool area is surrounded by wide concrete walks and features white metal fencing. The cozy glow from nearby windows hints at the welcoming ambiance of the adjoining house.

4.91 out of 5 average rating, 181 reviews

Charming home - views of Hunter Mountain slopes

FamilyLocationLayout

4.91 out of 5 average rating, 185 reviews

Home in Catskill

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

ValueLocationKitchen

4.92 out of 5 average rating, 112 reviews

Home in Hudson

Hudson River Sunset Getaway

LocationFamilySleep quality

4.93 out of 5 average rating, 126 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Chef’s Kitchen * Screened Porch * Near Woodstock

ValueLocationAir conditioning

Weekly house rentals

The image captures a scenic view of the property at sunset, highlighting the house surrounded by lush greenery. A tranquil pond reflects the warm hues of the sky, while a distant mountain looms softly in the background, adding to the area's natural beauty.

4.89 out of 5 average rating, 185 reviews

8 Bedroom Mountain Retreat with Barrel Sauna

ValueFamilyComfort

4.99 out of 5 average rating, 171 reviews

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

Valley View Chalet: AC, Hot Tub, Firepit, Games

ValueFamilyLayout

4.95 out of 5 average rating, 147 reviews

Home in Durham

Wow! Panoramic Mountain View, Minutes to Windham!

ValueFamilyAmenities

Home in Hunter Mountain Resort

A spacious deck features a glass-top dining table surrounded by four chairs, inviting outdoor dining. Lush greenery and rolling hills are visible in the background, complemented by a blue sky adorned with white clouds, creating a serene natural setting.

Pet Friendly, Close to Hiking and Mountain Lakes

LocationFamilyPets

4.96 out of 5 average rating, 129 reviews

5.0 out of 5 average rating, 246 reviews

Spend fall in style at #killercatmountainhouse

FamilyLocationEV charging

A hot tub is positioned on a wooden deck, with bubbling water visible. In the background, a barn and silos are seen against a clear blue sky. A pond reflects the greenery, with a few chairs placed nearby for relaxation.

4.97 out of 5 average rating, 115 reviews

Windham Farmhouse Escape

LocationFamilyWifi

4.98 out of 5 average rating, 198 reviews

A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.

Home in Cornwallville

Private Waterfall Retreat on 10 acres

ValueFamilyLayout

4.92 out of 5 average rating, 48 reviews

Home in East Jewett

Europe in The Catskills

LocationFamilyIndoor spaces

Private house rentals

A spacious living area features high wooden ceilings and large windows that provide abundant natural light. A comfortable sofa and armchairs are arranged around a central coffee table, while a television is mounted on a wooden wall. A dining area with a table for six is visible in the background.

4.94 out of 5 average rating, 94 reviews

Modern Ski House Minutes From The Slopes

FamilyValueHeating

The spacious living area is defined by a high wood-beamed ceiling and large windows that offer views of the surrounding greenery. A stylish pool table is centered in the room, surrounded by various seating options, including a sectional sofa in muted tones and accent chairs.

5.0 out of 5 average rating, 55 reviews

Family-ready retreat, games and BBQ

LocationFamilyBathroom

5.0 out of 5 average rating, 14 reviews

Home in Hensonville

Spacious Townhome for an Upstate getaway!

ValueFamilyGetting around

A modern kitchen is showcased with a large island featuring ample seating for six. Stainless steel appliances, including a refrigerator and a microwave, complement white cabinetry. Natural light enters through windows above the sink, highlighting the open space and wooden ceiling beam.

4.98 out of 5 average rating, 58 reviews

Beautifully restored 6 BR in the heart of Windham

FamilyLocationKitchen

A kitchen area is presented with wooden cabinetry and a glass-front display. A table surrounded by four wooden chairs is set for a meal, with a vase of flowers placed at the center. Natural light filters in through double glass doors leading to the outside.

4.92 out of 5 average rating, 74 reviews

Gods Country (3 bd) cottage

LocationFamilySkiing

5.0 out of 5 average rating, 16 reviews

The Mad Brook House | Walk to Main St, Windham

LocationFamilyCondition

4.97 out of 5 average rating, 37 reviews

ValueLocationHot tub