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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 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, (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
5 Aug - 6 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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 1,293 total
includes taxes & fees
26 Jul - 27 Jul
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Exterior

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 893
AED 2,138 total
includes taxes & fees
23 Aug - 24 Aug
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
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 2,269 total
includes taxes & fees
28 Jul - 29 Jul
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
TV, fireplace

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, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AED 937
AED 2,206 total
includes taxes & fees
27 Jul - 28 Jul
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 698
AED 1,936 total
includes taxes & fees
28 Jul - 29 Jul
Pines Vignette • Modern 3BR Home in Windham
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 595
AED 752 total
includes taxes & fees
6 Aug - 7 Aug
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
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 900
AED 2,206 total
includes taxes & fees
28 Jul - 29 Jul
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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 764
AED 1,603 total
includes taxes & fees
26 Jul - 27 Jul
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (14 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 1,582 total
includes taxes & fees
17 Aug - 18 Aug
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 579
AED 1,736 total
includes taxes & fees
28 Jul - 29 Jul
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Sauna

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 1,469
AED 2,547 total
includes taxes & fees
8 Aug - 9 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Indoor pool, a heated pool

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 2,459 total
includes taxes & fees
26 Jul - 27 Jul
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Smart TV, fireplace

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 576
AED 1,260 total
includes taxes & fees
5 Aug - 6 Aug
Cozy Waterfall Home | Close to All Mountains/Hikes
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.
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Smart TV, fireplace

A world where time stands still, close to Belleayre Ski & Wedding venues.

A world where time stands still, close to Belleayre Ski & Wedding venues.
City Roxbury
9.4 out of 10, Exceptional, (49 reviews)
"Rooms were clean, kitchen fully equipped. Enjoyed it a lot with my family. Will definitely go back"
United States
Anonymous traveler
The price is AED 479
AED 1,760 total
includes taxes & fees
6 Aug - 7 Aug
A world where time stands still, close to Belleayre Ski & Wedding venues.
Property grounds

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, (11 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
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

Starlite Motel

Starlite Motel

10/10 Excellent
"Very nice for the price. The full kitchen was great stocked with plates, glasses, pans etc. The beds seemed new and very comfortable and the bathroom was brand new and exceptionally nice. They have definitely been putting effort into updating the rooms and it shows. I would definitely stay there again."
Sean 2-night trip
Posted 8 hours ago
Starlite Motel