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Compare 38 Chalets in Ashland with updated reviews, rates, and availability.

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

10.0 out of 10, Exceptional, (11)
"Absolutely perfect weekend getaway. The house offered plenty of space for our group of 10. The fireplace made it so cozy. With the current outdoor burn ban, we didn't get to enjoy the firepit but the property was beautiful and scenic. The host was very easy to communicate with and very responsive. Definitely recommend!waybto c"
The price is AED 1,649
AED 3,037 total
includes taxes & fees
24 Nov - 25 Nov
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (39)
"The house has anything you want . A private house nice town . Quite,"
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (157)
"Another fabulous stay at our favorite VRBO! This mountain chalet never disappoints whether it’s just my husband and me staying for a weekend or when we bring our kids and pups for an extended stay! We love the location, centrally located for hiking trails, shopping antiques, restaurants, and so much more! Highly recommend a stay! The chalet is beautiful and has everything you need! The kitchen is equipped with all essentials, is always neat and clean, beds are freshly made and there are plenty...
Mountain Chalet with Breathtaking Panoramic Views

Catskill Chalet: Serene Mountain Escape

10.0 out of 10, Exceptional, (11)
"We wanted to spend a few days skiing at Belleayre and the house is conveniently located just a few minutes drive away. The premises were very clean and provided all of the comfort we needed during our staying. The pantry was nicely stocked and the kitchen had plenty of appliances to cook a storm if we wanted to. Room for improvement consists of better beds/mattresses (I know it is subjective but the twin bed is really too soft and the single ones weren't any better) and more tableware....
Catskill Chalet: Serene Mountain Escape

Rustic Mountain view Cabin 5 mins to Ski Area!

10.0 out of 10, Exceptional, (3)
"I really enjoyed our stay at the chateau. Everything went smoothly and the place was well put together. There were a couple communication mishaps, but I think that was more related to the app than anything. Joseph was incredibly responsive and helpful throughout the whole weekend. I have definitely noted this place for a return visit in the winter!"
Rustic Mountain view Cabin 5 mins to Ski Area!

Beautiful Windham Chalet 2 minutes to Town and the Mountain

3.0 star property
Beautiful Windham Chalet 2 minutes to Town and the Mountain

Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

10.0 out of 10, Exceptional, (20)
"I booked the Hirox for a special restorative women’s wellness retreat centered around slowing down and immersing ourselves in the beautiful fall colors and mountain views. This place was absolutely perfect. Everything was clean, the kitchen so well stocked, and it was truly obvious how much thought and intention went into designing this lovely home. Joshua was so helpful in planning our weekend and was extremely responsive all the way through the booking process and our stay. I would absolutely...
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!

10.0 out of 10, Exceptional, (17)
"Great location, lots of local hiking, beautiful area. House had a ton to offer for the kids, but we spent most of the time outside! Hosts very quick to respond and included thoughtful extras for our dogs. Highly recommend!"
Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!

Beautiful Chalet, mins to Hunter/Windham slopes

10.0 out of 10, Exceptional, (9)
"Really lovely house with a beautiful view."
Beautiful Chalet, mins to Hunter/Windham slopes

Never Lonesome Woodland Valley: Cozy 2bd Cottage!

9.8 out of 10, Exceptional, (8)
"I LOVE the rustic experience, as long as certain comforts are available. This cottage was the perfect balance, providing us the freshness of the creekside and all its wild greenery, some bugginess, and a clean place to rest that wasn’t overly sterile and bland. In fact, I found the furnishings to be very thoughtful, simple and pleasing; the kitchen and bathroom were well, but not overly, stocked; there was no clutter or worry that my small dog could get into anything he shouldn’t. This is easily...
Never Lonesome Woodland Valley: Cozy 2bd Cottage!

Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup

10.0 out of 10, Exceptional, (6)
"We like to meet up with some friends from Maine about once a year near the halfway point between us. Ray's Chalet is a great place to chill out and relax with friends and family. The Chalet is very clean and there's plenty of room for everybody. Great for grilling, lawn games, bonfires, etc. Ray adds a lot of nice touches as well, but I won't ruin the surprises for you. (BTW--Ray, thanks for the spare toothbrush set up! Saved our lives when we had to bring the kids at the last minute due to...
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup

FALL FOLIAGE & WINTER SKI Getaway w PRIVATE Indoor Pool. 5 mins to Hunter Mtn!

8.4 out of 10, Very Good, (52)
"Overall, nice private location. House was not as clean as it could have been . Owner responsive to messages and requests!"
FALL FOLIAGE & WINTER SKI Getaway w PRIVATE Indoor Pool. 5 mins to Hunter Mtn!

Cozy Silo with Sunset Mountain Views

9.6 out of 10, Exceptional, (4)
"We had a nice time and would likely come again. Just two nitpicks: 1) the mattresses are extremely smushy and two people in our party had back issues. 2) the hot water runs out fast so one person had to take a cold shower. Overall, nice home in the woods. Thank you "
Cozy Silo with Sunset Mountain Views

🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀

10.0 out of 10, Exceptional, (21)
"We had a great weekend at the Manor. The game room was excellent and provided entertainment for everyone."
🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀

Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed

10.0 out of 10, Exceptional, (8)
"Relaxing remote location with lovely views of local farmland. Perfect wedding weekend getaway with our adult kids."
The price is AED 1,543
AED 3,874 total
includes taxes & fees
6 Dec - 7 Dec
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed

Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

Never Lonesome Hunter: Smart 4bd Getaway near Mtn

10.0 out of 10, Exceptional, (2)
"Nice little house to stay in if you're looking to spend time in the mountains. It's old, for sure, but it was comfortable and conveniently located. Hosts were great about communicating. It was a nice, chill vacation."
Never Lonesome Hunter: Smart 4bd Getaway near Mtn

Windham Immaculate Ski Chalet with Awesome Fire Pit.

9.8 out of 10, Exceptional, (8)
"Our family really enjoyed this home over a long fall weekend. The home is immaculate with plenty of space/bathrooms for my 3 adult kids and my husband and I. The kitchen is well stocked with everything needed. Plenty of paper products, soaps, basic spices. I appreciated how clean it was. Communication with the host was great, very responsive. We thoroughly enjoyed both the indoor fireplace and outdoor fire pit. Beautiful area for long hikes and to enjoy everything Windham has to offer. Would...
Windham Immaculate Ski Chalet with Awesome Fire Pit.

Chalet near Windham w/ hot tub

Chalet near Windham w/ hot tub

Gorgeous 3 bedroom minutes from Belleayre

Gorgeous 3 bedroom minutes from Belleayre
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Ashland

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is AED 459
AED 525 total
includes taxes & fees
27 Nov - 28 Nov
Starlite Motel

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.