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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ashland vacation homes

A two-story building with large windows and a storefront.

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
8.8 out of 10, Excellent, (65 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is AED 404
AED 718 total
includes taxes & fees
2 Nov - 3 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

2. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AED 735
AED 1,964 total
includes taxes & fees
9 Nov - 10 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A wooden cabin interior with a central wood-burning stove, a bench with a bear pillow, and a window with a view of the outdoors.

3. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (77 reviews)
"Great stay highly recommend!"
United States
Shannon H.
Mountain house with Scandinavian BBQ hut and Hot tub
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

4. Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
Windham
10.0 out of 10, Exceptional, (1 review)
"My stay was very short but we maximized our time by enjoying the properties endless offerings. Lots of things to do and board games were available. Plenty of room and beds every one. View from jacuzzi was phenomenal to see the stars at night. I’d recommend definitely and will revisit during winter"
United States
Lobid C.
The price is AED 730
AED 2,728 total
includes taxes & fees
25 Oct - 26 Oct
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A bedroom with a bed, a desk, a chair, a ceiling fan, and two windows.

5. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is AED 1,206
AED 2,571 total
includes taxes & fees
3 Nov - 4 Nov
Catskills Escape w/ Hot Tub & Fireplace
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

6. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is AED 735
AED 1,964 total
includes taxes & fees
26 Oct - 27 Oct
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

7. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is AED 349
AED 1,329 total
includes taxes & fees
27 Oct - 28 Oct
West Kill Barnhouse: Ski, Work & Unwind
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

8. Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is AED 1,653
AED 3,741 total
includes taxes & fees
9 Nov - 10 Nov
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

9. Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (12 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

10. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
Midnight Fox
A house with a fire pit and outdoor seating.

11. The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic property. Especially good for families or groups. So much to do right on property, almost no need to leave. Place was exactly as described."
United States
David H.
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

12. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is AED 702
AED 1,944 total
includes taxes & fees
19 Nov - 20 Nov
Pines Vignette • Modern 3BR Home in Windham
A wooden cabin with a porch, two chairs, and a table.

13. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Halcott Center
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect during my stay. The service was excellent, and everything went very smoothly. I’m really happy with the overall experience and would highly recommend it to anyone."
United States
Hnin
The price is AED 436
AED 1,594 total
includes taxes & fees
8 Nov - 9 Nov
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
A hot tub on a wooden deck with a view of trees and a clear sky.

14. Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
The price is AED 1,322
AED 3,320 total
includes taxes & fees
25 Oct - 26 Oct
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
A fire pit with two chairs in a backyard.

15. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is AED 1,417
AED 2,447 total
includes taxes & fees
3 Nov - 4 Nov
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
A covered outdoor area with a sofa, a table with a grill, and a tripod-mounted camera.

16. Gorgeous Mountains Views & Private Stream in Secluded Oasis

Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gilboa
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was great: attentive host, comfortable lodgings, beautiful setting."
United States
Carrie S.
The price is AED 661
AED 1,543 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous Mountains Views & Private Stream in Secluded Oasis
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

17. Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is AED 764
AED 1,615 total
includes taxes & fees
25 Oct - 26 Oct
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

18. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (16 reviews)
"The location was perfect, and the view of Hunter Mountain was beautiful. Our stay was enjoyable for travelers of all ages."
United States
Allyson R.
The price is AED 1,405
AED 2,620 total
includes taxes & fees
25 Oct - 26 Oct
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A building with a red roof, surrounded by a grassy area with yellow flowers and a large tree.

19. 2BR Mountain View Home with Pool & 3 mins to Ski Slopes

2BR Mountain View Home with Pool & 3 mins to Ski Slopes
Tannersville
9.8 out of 10, Exceptional, (97 reviews)
"Great location, house is a bit run down. If you’re there just for skiing, this would be a great home."
United States
Murodjon R.
The price is AED 504
AED 1,370 total
includes taxes & fees
1 Nov - 2 Nov
2BR Mountain View Home with Pool & 3 mins to Ski Slopes
A covered porch with a bench and a table, a door leading inside, and a railing with lights.

20. LOCATION! LOCATION!! WALK TO FESTIVALS AND HUNTER MOUNTAIN!!!!

LOCATION! LOCATION!! WALK TO FESTIVALS AND HUNTER MOUNTAIN!!!!
Lanesville
10.0 out of 10, Exceptional, (27 reviews)
"Excellent location, smooth check-in process, well maintained clean house with all necessities. Thank you!"
United States
Nikolai
The price is AED 992
AED 1,880 total
includes taxes & fees
24 Oct - 25 Oct
LOCATION! LOCATION!! WALK TO FESTIVALS AND HUNTER MOUNTAIN!!!!
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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Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Good Staff"
Siva Kumar 3-night trip
Posted 9 hours ago
Hotel Vienna