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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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 817 total
includes taxes & fees
26 Aug - 27 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
2 Sep - 3 Sep
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
TV, fireplace

3. 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 826
AED 2,087 total
includes taxes & fees
14 Sep - 15 Sep
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 569
AED 1,611 total
includes taxes & fees
23 Aug - 24 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 1,361 total
includes taxes & fees
31 Aug - 1 Sep
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
2 Sep - 3 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 882
AED 2,198 total
includes taxes & fees
14 Sep - 15 Sep
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Interior

8. 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
Exterior

9. 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 863
AED 2,154 total
includes taxes & fees
9 Sep - 10 Sep
Pines Vignette • Modern 3BR Home in Windham
Smart TV, books, stereo, computer monitors

10. 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
24 Aug - 25 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
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!
Sauna

12. 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
23 Aug - 24 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Interior

13. 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 988
AED 2,083 total
includes taxes & fees
23 Aug - 24 Aug
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
Children's area

14. 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 1,365 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Interior

15. 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 486
AED 1,168 total
includes taxes & fees
31 Aug - 1 Sep
Cozy Waterfall Home | Close to All Mountains/Hikes
TV, fireplace, stereo

16. 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 2,818 total
includes taxes & fees
1 Sep - 2 Sep
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Property grounds

17. 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, (13 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
The price is AED 2,747
AED 4,637 total
includes taxes & fees
24 Aug - 25 Aug
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Smart TV, fireplace, books

18. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is AED 1,405
AED 2,640 total
includes taxes & fees
23 Aug - 24 Aug
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Dining

19. Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home

Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home
East Jewett
10.0 out of 10, Exceptional, (7 reviews)
"My family and I had a wonderful experience at this property. The house was clean, nicely decorated and had everything you need to feel at home! Jeff, the host , was so helpful and accommodating. We will definitely be back!"
United States
Beth C.
The price is AED 1,968
AED 3,575 total
includes taxes & fees
20 Sep - 21 Sep
Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home
Interior

20. Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15

Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
West Kill
10.0 out of 10, Exceptional, (1 review)
"It was a great spot for all three generations to be together for the holiday. House was clean and close to lots of hikes. Hosts were available."
United States
Kate R.
The price is AED 1,967
AED 4,524 total
includes taxes & fees
3 Sep - 4 Sep
Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Employees were very courteous and helpful Outside grounds could use more lighting"
Abraham j 2-night trip
Posted 12 hours ago
Hunter Lodge, a Bluebird by Lark