Default HTG hotel image

Holiday Homes in Ashland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ashland holiday homes

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, (59 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is €191
includes taxes & fees
14 Jun - 15 Jun
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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, (3 reviews)
"Excellent place, we loved the house and it had everything we needed to avoid getting out of the house since we had to go after a snowstorm. A very homey house and the hosts were very attentive and responded very quickly to our inquiries."
United States
Monica O.
The price is €563
includes taxes & fees
22 Jun - 23 Jun
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

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
9.6 out of 10, Exceptional, (46 reviews)
"This was a fantastic stay in a beautiful cabin with close access to Belleayre!"
United States
Neil V.
The price is €390
includes taxes & fees
18 Jun - 19 Jun
A world where time stands still, close to Belleayre Ski & Wedding venues.

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 €281
includes taxes & fees
14 Jun - 15 Jun
Cozy Waterfall Oasis + Firepit

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, (3 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 €338
includes taxes & fees
12 Jun - 13 Jun
2-bedroom in Peaceful Middleburgh Vroman’s Nose View

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 €317
includes taxes & fees
15 Jun - 16 Jun
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Cozy Home, Wood-burning Fireplace, Ski Belleayre

Cozy Home, Wood-burning Fireplace, Ski Belleayre
Margaretville
9.8 out of 10, Exceptional, (17 reviews)
"We only got to stay for one night, but it was lovely, and large! Excellent kitchen equipment, and really close to Belleayre. We'll be back!"
United States
Jack R.
Cozy Home, Wood-burning Fireplace, Ski Belleayre

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 traveller
The price is €352
includes taxes & fees
16 Jun - 17 Jun
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

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 €374
includes taxes & fees
14 Jun - 15 Jun
Midnight Fox

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 €407
includes taxes & fees
14 Jun - 15 Jun
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail
Hobart
10.0 out of 10, Exceptional, (127 reviews)
"We loved our stay. The house was clean and generously stocked."
United States
Amy W.
Cozy Country Farmhouse Along the Catskill Scenic Trail

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 €459
includes taxes & fees
1 Jul - 2 Jul
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!

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 €739
includes taxes & fees
14 Jun - 15 Jun
Fox Hollow at Carter Bridge Estate

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (40 reviews)
"Excellent location close to everything we needed. The property was clean and comfortable, and the WiFi was strong and dependable throughout our stay."
United States
Jessica P.
The price is €321
includes taxes & fees
14 Jun - 15 Jun
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace
Tannersville
The price is €564
includes taxes & fees
16 Jun - 17 Jun
Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

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 €363
includes taxes & fees
16 Jun - 17 Jun
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (4 reviews)
"House had everything, very clean, host very responsive, located close to everything. Great family vacation!"
United States
Jaylyn B.
The price is €731
includes taxes & fees
14 Jun - 15 Jun
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

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 €772
includes taxes & fees
16 Jun - 17 Jun
Hot Tub • Pool Table • Fire Pit • Game Room •Views - Holiday Home

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 €469
includes taxes & fees
14 Jun - 15 Jun
2 Min Walk to Windham Town | Hot Tub | Fire Pit

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 €438
includes taxes & fees
7 Jul - 8 Jul
Pines Vignette • Modern 3BR Home in Windham
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
400
Accommodation
553 Holiday Homes
Lowest Price
€191
Highest Price
€772