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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 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 813 total
includes taxes & fees
30 Aug - 31 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Interior

2. 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 606
AED 1,654 total
includes taxes & fees
8 Sep - 9 Sep
West Kill Barnhouse: Ski, Work & Unwind
Exterior

3. 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

4. Escape the City. Discover the Heart of the Catskills.

Escape the City. Discover the Heart of the Catskills.
West Kill
10.0 out of 10, Exceptional, (2 reviews)
"If you've lived in an old house before, then you know what to expect. It was good for our needs during our short stay. The house is spacious and there is lots of light. The beds were comfortable and the water pressure was awesome. There is an a/c in every upstairs bedroom."
United States
Alexandra I.
The price is AED 1,306
AED 2,926 total
includes taxes & fees
29 Aug - 30 Aug
Escape the City. Discover the Heart of the Catskills.
TV, fireplace, video games, stereo

5. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is AED 793
AED 2,149 total
includes taxes & fees
9 Sep - 10 Sep
Catskills Escape w/ Hot Tub & Fireplace
TV, fireplace

6. 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 771
AED 2,019 total
includes taxes & fees
14 Sep - 15 Sep
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Property grounds

7. 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 1,353 total
includes taxes & fees
31 Aug - 1 Sep
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Property grounds

8. 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 794 total
includes taxes & fees
1 Sep - 2 Sep
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Dining

9. 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 808
AED 2,110 total
includes taxes & fees
14 Sep - 15 Sep
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Interior

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.
The price is AED 841
AED 1,651 total
includes taxes & fees
9 Sep - 10 Sep
Midnight Fox
Outdoor dining

11. '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 Mountain House:' Windham Retreat w/ Hot Tub!
Exterior

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 790
AED 2,051 total
includes taxes & fees
10 Sep - 11 Sep
Pines Vignette • Modern 3BR Home in Windham
Smart TV, books, stereo, computer monitors

13. 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.
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior

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

Entire Renovated Country House, Sleeps 7, Pets, EV, 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 1,980
AED 3,305 total
includes taxes & fees
30 Aug - 31 Aug
Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
Sauna

15. 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 2,563 total
includes taxes & fees
30 Aug - 31 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Indoor pool, a heated pool

16. 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 2,416 total
includes taxes & fees
30 Aug - 31 Aug
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Smart TV, fireplace

17. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (17 reviews)
"Everything was perfect!"
United States
Jen C.
The price is AED 468
AED 1,168 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Waterfall Oasis + Firepit
Children's area

18. 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, (2 reviews)
"Friendly host accommodated all our requests. House is quaint and well-kept and well-stocked for all possible needs."
United States
Simon R.
The price is AED 463
AED 1,361 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
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 2,700 total
includes taxes & fees
7 Sep - 8 Sep
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Interior

20. Spacious, stylish barn and Private Creek, Firepit

Spacious, stylish barn and Private Creek, Firepit
Denver
The price is AED 636
AED 1,608 total
includes taxes & fees
20 Sep - 21 Sep
Spacious, stylish barn and Private Creek, Firepit
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 Mountain Brook

Hotel Mountain Brook

10/10 Excellent
"Very cute place. Mountains air. Yummy breakfast"
Ann 2-night trip
Posted 2 hours ago
Hotel Mountain Brook