Town of Ashland Rentals
From $371 per night (USD)VRBO
Creek house with expansive mountain views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our creek house with expansive mountain views and open lush fields. After a long day of hiking, fishing, bike ...
From $371 per night (USD)VRBO
From $828 per night (USD)Expedia
Private Manor Catskills - Windham | 6BR, 4 BA, Pool, Hot Tub & Cinema, Gardens
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
LISTING DESCRIPTION A private six-bedroom estate offering upscale comfort and luxury. The property is part of the Dingl ...
From $828 per night (USD)Expedia
From $425 per night (USD)VRBO
Holly Lodge - Ski Windham, Hunter, Catskills
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to Holly Lodge in Windham, NY, recently renovated house that has the thoughtful charm to be your home a ...
From $425 per night (USD)VRBO
From $882 per night (USD)VRBO
CLARKS NEST
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Great 4 acre Hideaway is set back off the road. A secluded 4 bedroom, 3 bath cabin boasts an open concept living, d ...
From $882 per night (USD)VRBO
From $352 per night (USD)VRBO
Magical Home Located in Windham and Catskills
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Let this Magical Home take you away to your special place in the Catskills. Located nearby the town of Windham and less ...
From $352 per night (USD)VRBO
From $953 per night (USD)Expedia
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Wonderful in Windham Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests, ample outdoor seating, ...
From $953 per night (USD)Expedia
From $253 per night (USD)VRBO
NEW HOT TUB! Game Room • Firepit • Near Windham
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recently renovated with a brand-new patio and private 6-person hot tub, this charming 4-bedroom, 2-bath mountain retreat ...
From $253 per night (USD)VRBO
From $789 per night (USD)Expedia
NEW LISTING! Bright & Inviting 4 BR chalet in Windham. 2 miles to slopes.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Get comfy at this charming, family-friendly chalet in Windham. With 4 bedrooms (1 king, 1 queen, and 4 bunk beds) and 2. ...
From $789 per night (USD)Expedia
From $454 per night (USD)VRBO
Catskills Mountain Home Near Windham w/ Fireplace & Open Living | Deer Run Lodge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Deer Run Lodge, a warm and inviting Catskills getaway designed for comfort, connection, and easy mountain liv ...
From $454 per night (USD)VRBO
From $1647 per night (USD)Expedia
Modern Forest Retreat with Hot Tub and Sauna - Entire Magda Cabin XL!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
About this space This spacious, serene and secluded chalet is a newly renovated seven bedroom five bathroom luxury pro ...
From $1647 per night (USD)Expedia
From $716 per night (USD)VRBO
NEW! Farmhouse Mountain View’s,FireplaceGrill, Pet-Friendly, Soaking Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Slow down and savor the beauty of fall at The Maeve House, a newly renovated 1800s Catskills farmhouse. Sip your morning ...
From $716 per night (USD)VRBO
From $669 per night (USD)VRBO
A-Frame 4-bedroom cottage with AC in charming Windham
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Your Windham adventure begins at this wonderful 4-bedroom cottage. Inside, guests find a cozy mix of beds including a ki ...
From $669 per night (USD)VRBO
From $416 per night (USD)VRBO
Amazing Chic Cabin with Private Backyard, Deck and Jacuzzi in New York
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 10
Welcome to our recently renovated house that has the thoughtful charm to be your home away from home, but also includes ...
From $416 per night (USD)VRBO
From $441 per night (USD)VRBO
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this peaceful mountain retreat in the Catskills, the Windham Chalet. Windham is know as the “Gem of the Catski ...
From $441 per night (USD)VRBO
From $805 per night (USD)VRBO
Casa Magda: Catskills | Hot Tub | Swimming | Hiking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Relax and recharge at Casa Magda, a design-forward retreat on 9 private acres in Windham, NY, just 2.5 hours ...
From $805 per night (USD)VRBO
From $316 per night (USD)VRBO
Charming Ashland Cottage on 5+ acres—minutes to Windham Mountain
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This retreat, located on over 5 private acres, is just 10 minutes to downtown Windham’s restaurants, bars, local shops a ...
From $316 per night (USD)VRBO
From $759 per night (USD)VRBO
Windham Pines Lodge & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Split level home with Hot Tub and Outdoor Firepit. Conveniently located on private road just 5 miles from Windham Ski ar ...
From $759 per night (USD)VRBO
From $541 per night (USD)VRBO
DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Tucked away on 110 acres of stunning Catskill Mountain landscape, this charming log cabin awaits any family looking for ...
From $541 per night (USD)VRBO
From $226 per night (USD)VRBO
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This is a comfy 3-bedroom cottage perfect for unwinding with friends and family. It is small, cozy, and has a wonderful ...
From $226 per night (USD)VRBO
From $670 per night (USD)VRBO
The Serene Gem! 10 min to Windham! 20 min to Hunter!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our vacation gem! Specious and bright, surrounded by woods, with great views, located 10 min to Windham, 20 ...
From $670 per night (USD)VRBO
From $463 per night (USD)VRBO
Ready for your family if you need a retreat.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
6 minutes to the base of the mountain sits a cozy little 3 bedroom, 2 bath log cabin with a large loft that overlooks th ...
From $463 per night (USD)VRBO
From $367 per night (USD)Expedia
Firepit, Cozy Farmhouse & Adventure Nearby | Catskill Park Farm by AvantStay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Catskill Park Farm, your Windham escape where rustic charm meets modern comfort on a sprawling, secluded lot. ...
From $367 per night (USD)Expedia
From $287 per night (USD)VRBO
Delightful 3-bedroom chalet with WiFi in Windham
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This fabulous chalet in Windham offers a cozy retreat for guests. With 3 bedrooms including a queen, twin, and bunk bed, ...
From $287 per night (USD)VRBO
From $1265 per night (USD)VRBO
Windham Mountain Escape - 5bd/4ba Private Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to the Catskills and visit this Windham Mountain Home. Stay in this 2 floor, 5 bedroom, 4 bathroom house on a pr ...
From $1265 per night (USD)VRBO
From $696 per night (USD)VRBO
Grand Windham Retreat w/ Fire Pit & Game Room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Leave all your troubles behind and let the fresh air at this Windham vacation rental take over! This 2-bedroom, 2-bathro ...
From $696 per night (USD)VRBO
From $675 per night (USD)VRBO
Ashland · Home Theatre, Game Room, Private Driving Range
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
House sits on 17 private acres in the picturesque Catskill Mountains, Ashland, NY. The house offers four-season fun with ...
From $675 per night (USD)VRBO
From $257 per night (USD)VRBO
Seasonal rental: Pet friendly home near Windham and Hunter Ski Resorts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New, three bedroom, two bath home on three acres, conveniently located a 10 minute/5 mile drive from Windham Ski Mountai ...
From $257 per night (USD)VRBO
From $732 per night (USD)Expedia
(New Listing) Beautiful mountain home on private road
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Newly Listed!! Beautiful mountain home located on a quite private road. This is a large 5 bedroom home only a few minute ...
From $732 per night (USD)Expedia
From $1145 per night (USD)VRBO
Catskills Retreat with Theater, Hot Tub and Games
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 22
Bring everyone together at Bella Vista — an entertainment-focused Catskills retreat designed for large groups, multiple ...
From $1145 per night (USD)VRBO
From $640 per night (USD)Expedia
Catskills Escape w/ Hot Tub & Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to a fully equipped Catskills retreat, ideal for remote work or true unwinding. Three ethernet workspaces, a sun- ...
From $640 per night (USD)Expedia
From $1058 per night (USD)VRBO
Majestic estate in the mountains, over two acres of park-like land,...
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Hilltop Mountain Home Majestic estate in the mountains, over two acres of park-like land, secluded, gorgeous mountain v ...
From $1058 per night (USD)VRBO
From $824 per night (USD)Expedia
Luxury Forest Villa - 6BDRM, 4BTHRM | Hot Tub & Movie Room, Windham 10min
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
PROPERTY DESCRIPTION ...
From $824 per night (USD)Expedia
From $517 per night (USD)VRBO
Red Fox Townhouse & alpine spa hot tub, fire pit & BBQ grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Red Fox Townhouse is located in Windham! ...
From $517 per night (USD)VRBO
From $399 per night (USD)Expedia
Private 7-Acre Retreat: On-Site Pond, Streams
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Seeking some peace and quiet? You’ll find it all, plus stunning views and outdoor entertainment, at this Jewett vacation ...
From $399 per night (USD)Expedia
From $253 per night (USD)VRBO
Spacious Rental for Group Vacaton with Waterfall Views near Catskills Region, New York
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 10
This rental has everything guests will need for a group vacation in the Catskills Region of New York. Built in the late ...
From $253 per night (USD)VRBO
From $1108 per night (USD)VRBO
Stunning Views Movie Theater and Next To Skiing
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 9
Disconnect to reconnect. Perched on a private peak in the Hudson Valley, The Hilltop Sanctuary is a 27-acre design-forwa ...
From $1108 per night (USD)VRBO
From $1094 per night (USD)VRBO
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to a wonderful oasis of tranquility. Beautiful bright A-frame home sited on 10 secluded private acres with open ...
From $1094 per night (USD)VRBO
From $689 per night (USD)VRBO
SaltBox Lodge: Windham | Privacy | Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: SaltBox Lodge is an enchanting 4 bed, 3 bath mountain cabin under 3hrs from NYC, just 6 mins from Windham Moun ...
From $689 per night (USD)VRBO
From $454 per night (USD)VRBO
Windham Mountain Condo with Deck & Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your cozy Windham mountain escape, perfectly located just 1 mile from Windham Mountain. This inviti ...
From $454 per night (USD)VRBO
From $701 per night (USD)Expedia
Unwind Windham, Chalet
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
<p>Welcome to <strong>Unwind Windham</strong>, a stunning mountain chalet designed for relaxation and adventure. </p> ...
From $701 per night (USD)Expedia
From $1038 per night (USD)VRBO
Luxury waterfront ski cabin, 4-bedroom house and office
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
House Details: — Covered front porch with breathtaking lakefront and mountain range views, a gas barbecue, and ski/snow ...
From $1038 per night (USD)VRBO
From $3365 per night (USD)Expedia
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen ...
From $3365 per night (USD)Expedia
From $625 per night (USD)VRBO
Alpine View - Hot Tub, Rustic Charm, Mountain Views & Sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Alpine View is a charming two story 4 bed, 3 bath chalet 3 hours away from NYC. This home features gorgeous mo ...
From $625 per night (USD)VRBO
From $322 per night (USD)Expedia
Fantastic 2 family vacation home with EV charger
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The perfect luxury vacation gettaway! Fully equipped with everything you need to relax after a day out. Minutes from Win ...
From $322 per night (USD)Expedia
From $2296 per night (USD)VRBO
*The View* ski in/out modern luxury at Windham Mountain Resort
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
The View is a spectacular new house at the top of Windham Mountain. Ease of ski in/out with all the amenities, from expa ...
From $2296 per night (USD)VRBO
From $1271 per night (USD)Expedia
Birch Hill - Luxury Mountain Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Newly renovated quiet luxury retreat, close to town, the slopes, golf and hiking. The best skiing, riding and hiking in ...
From $1271 per night (USD)Expedia
From $306 per night (USD)VRBO
Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in a wood-fired hot tub under the stars on 7 private acres. Cozy firepit, stargazing, and easy access to Catskill ...
From $306 per night (USD)VRBO