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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Ashland vacation homes

Exterior

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
9.0 out of 10, Wonderful, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is AED 477
AED 809 total
includes taxes & fees
13 Aug - 14 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

2. Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is AED 600
AED 2,100 total
includes taxes & fees
1 Sep - 2 Sep
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Interior

3. Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"
United States
Timothy M.
The price is AED 625
AED 1,635 total
includes taxes & fees
16 Aug - 17 Aug
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
Interior

4. 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 1,337 total
includes taxes & fees
13 Aug - 14 Aug
West Kill Barnhouse: Ski, Work & Unwind
Property grounds

5. 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, (10 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.
The price is AED 661
AED 1,313 total
includes taxes & fees
13 Aug - 14 Aug
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Property grounds

6. Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is AED 615
AED 788 total
includes taxes & fees
1 Sep - 2 Sep
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Dining

7. 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 1,028
AED 2,380 total
includes taxes & fees
25 Aug - 26 Aug
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Exterior

8. 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 679
AED 1,928 total
includes taxes & fees
8 Sep - 9 Sep
Pines Vignette • Modern 3BR Home in Windham
TV, fireplace

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AED 973
AED 2,265 total
includes taxes & fees
13 Aug - 14 Aug
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Sauna

10. 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, (73 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is AED 1,488
AED 2,582 total
includes taxes & fees
25 Aug - 26 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Smart TV, books, stereo, computer monitors

11. Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
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 1,623 total
includes taxes & fees
13 Aug - 14 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Exterior

12. 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 464
AED 1,639 total
includes taxes & fees
10 Sep - 11 Sep
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Interior

13. 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.
The price is AED 841
AED 1,651 total
includes taxes & fees
17 Aug - 18 Aug
Midnight Fox
Outdoor dining

14. 'The Mountain House:' Windham Retreat w/ Hot Tub!

'The Mountain House:' Windham Retreat w/ Hot Tub!
Windham
10.0 out of 10, Exceptional, (36 reviews)
"Great stay Very comfortable "
United States
Teresa G.
The price is AED 1,308
AED 2,971 total
includes taxes & fees
23 Aug - 24 Aug
'The Mountain House:' Windham Retreat w/ Hot Tub!
Indoor pool, a heated pool

15. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is AED 1,653
AED 2,495 total
includes taxes & fees
13 Aug - 14 Aug
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Interior

16. Cozy Waterfall Home | Close to All Mountains/Hikes

Cozy Waterfall Home | Close to All Mountains/Hikes
East Durham
10.0 out of 10, Exceptional, (3 reviews)
"The host is very responsive and the listing is accurate about what to expect with the property."
United States
John K.
The price is AED 531
AED 1,224 total
includes taxes & fees
13 Aug - 14 Aug
Cozy Waterfall Home | Close to All Mountains/Hikes
Children's area

17. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (1 review)
"House was clean and well kept, perfect for our family weekend trip!"
United States
Edward C.
The price is AED 463
AED 1,365 total
includes taxes & fees
13 Aug - 14 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Interior

18. Spacious, stylish barn and Private Creek, Firepit

Spacious, stylish barn and Private Creek, Firepit
Denver
The price is AED 703
AED 1,695 total
includes taxes & fees
14 Aug - 15 Aug
Spacious, stylish barn and Private Creek, Firepit
TV, fireplace, stereo

19. West Elm Lodge near Skiing • Waterfront • Groups • Breweries

West Elm Lodge near Skiing • Waterfront • Groups • Breweries
West Kill
9.8 out of 10, Exceptional, (11 reviews)
"Great home, great host and we enjoyed our time there. Will plan to stay there again next year!"
United States
dominick s.
The price is AED 1,296
AED 2,692 total
includes taxes & fees
17 Aug - 18 Aug
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Property grounds

20. Large Group Catskills Mountain Retreat near Hunter & Windham Mountains

Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Prattsville
10.0 out of 10, Exceptional, (12 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
The price is AED 2,747
AED 4,637 total
includes taxes & fees
25 Aug - 26 Aug
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
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

8/10 Good
"Overall, the stay was very nice for our 2 day getaway. The room was clean and spacious, and the pool was very nice and well maintained, and the staff was helpful. The breakfast was OK, with warm croissants/muffins, but the coffee machine idea needs to be reevaluated. It was acting up on the first day, and the wait for each single cup coffee was too much in the morning rush. A morning full pot (or pots) of coffee should be put out for the breakfast rush. And it would be nice to have decaf as an option. Otherwise, our stay was pleasant, and we would certainly come back."
Colleen 2-night trip
Posted 10 hours ago
Hotel Vienna