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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Ashland vacation homes

Exterior

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, (61 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
3 Aug - 4 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Property grounds

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 651
AED 823 total
includes taxes & fees
15 Jul - 16 Jul
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Smart TV, fireplace

Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.4 out of 10, Exceptional, (16 reviews)
"Everything was perfect!"
United States
Jen C.
The price is AED 554
AED 1,360 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Waterfall Oasis + Firepit
Property grounds

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 1,345 total
includes taxes & fees
15 Jul - 16 Jul
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Interior

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (12 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 1,586 total
includes taxes & fees
21 Jul - 22 Jul
Midnight Fox
Interior

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Durham
10.0 out of 10, Exceptional, (3 reviews)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
The price is AED 628
AED 1,813 total
includes taxes & fees
21 Jul - 22 Jul
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Exterior

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 680
AED 1,916 total
includes taxes & fees
20 Jul - 21 Jul
Pines Vignette • Modern 3BR Home in Windham
Exterior

Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail
Hobart
10.0 out of 10, Exceptional, (128 reviews)
"We loved our stay. The house was clean and generously stocked."
United States
Amy W.
The price is AED 643
AED 1,253 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Country Farmhouse Along the Catskill Scenic Trail
Coffee/tea maker, fridge, microwave, oven

2-bedroom in Peaceful Middleburgh Vroman’s Nose View

2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Middleburgh
10.0 out of 10, Exceptional, (4 reviews)
"Janelle was very welcoming and accommodating. The house was decorated for the holidays and very clean, comfy, and cozy. There are wonderful amenities such as pool, fire pit, grilling area, if the weather allows for outdoor activities. "
United States
Lisa C.
The price is AED 826
AED 1,427 total
includes taxes & fees
22 Jul - 23 Jul
2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Interior

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (5 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is AED 882
AED 2,670 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Smart TV, fireplace

Fox Hollow at Carter Bridge Estate

Fox Hollow at Carter Bridge Estate
East Durham
10.0 out of 10, Exceptional, (2 reviews)
"The unit was extremely clean,nice, everything we needed for a great time it was well stocked with all you needed close to town. Getting in touch with checking in was as easy as it could be. I would definitely visi again. Than you"
United States
Matthew E.
The price is AED 793
AED 3,019 total
includes taxes & fees
27 Jul - 28 Jul
Fox Hollow at Carter Bridge Estate
Fridge, microwave, oven, stovetop

Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard

Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard
Tannersville
The price is AED 893
AED 2,309 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard
Smart TV, books, stereo, computer monitors

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 813
AED 1,663 total
includes taxes & fees
20 Jul - 21 Jul
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior

Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount

Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount
Pine Hill
10.0 out of 10, Exceptional, (1 review)
"The host were great communicating with us and answered all our questions. The house was super cute, well equipped with anything we needed (towels, kitchen appliances, dishes, coffee maker, etc)We would definitely stay again if we are in the area "
United States
Patricia F.
The price is AED 1,102
AED 2,082 total
includes taxes & fees
10 Aug - 11 Aug
Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount
2 bedrooms, free WiFi, bed sheets

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Arkville
9.8 out of 10, Exceptional, (27 reviews)
"We are so happy we had a peaceful and relax time we love the sauna what a great place "
United States
Christian
The price is AED 929
AED 1,838 total
includes taxes & fees
15 Jul - 16 Jul
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Exterior

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 750
AED 2,285 total
includes taxes & fees
26 Jul - 27 Jul
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Dining

Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit

Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
Tannersville
8.8 out of 10, Excellent, (6 reviews)
"The house was great! We enjoyed shopping, hiking and going to local restaurants. The house was exactly as described. Very comfortable. Ivan was a great host. Will definitely stay again."
United States
Kathleen D.
The price is AED 992
AED 2,459 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
Smart TV

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
10.0 out of 10, Exceptional, (1 review)
"Very clean; loved the spacious living room/kitchen/ dining area. Hope to stay here again. "
United States
Anonymous traveler
The price is AED 1,179
AED 1,773 total
includes taxes & fees
15 Jul - 16 Jul
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
TV, fireplace, stereo

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 1,335
AED 2,827 total
includes taxes & fees
15 Jul - 16 Jul
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Dining

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 753
AED 2,015 total
includes taxes & fees
15 Jul - 16 Jul
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"We enjoyed the pool and hot tubs"
Caroline 2-night trip
Posted 18 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts