Default HTG hotel image

Search Vacation 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 vacation homes

Modern getaway in Catskills

Modern getaway in Catskills
Cairo
10.0 out of 10, Exceptional, (13 reviews)
"The host was accommodating and the house was very nice!"
United States
Ken B.
The price is AED 2,020
AED 3,470 total
includes taxes & fees
21 Jun - 22 Jun
Modern getaway in Catskills

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 AED 591
AED 1,345 total
includes taxes & fees
21 Jun - 22 Jun
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

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.
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 AED 425
AED 1,201 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Waterfall Oasis + Firepit

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 694
AED 1,500 total
includes taxes & fees
24 Jun - 25 Jun
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

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, (60 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is AED 478
AED 801 total
includes taxes & fees
21 Jun - 22 Jun
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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
22 Jun - 23 Jun
Midnight Fox

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 1,357 total
includes taxes & fees
22 Jun - 23 Jun
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

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, (4 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is AED 973
AED 2,527 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

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 AED 826
AED 1,415 total
includes taxes & fees
21 Jun - 22 Jun
2-bedroom in Peaceful Middleburgh Vroman’s Nose View

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)
The price is AED 595
AED 1,753 total
includes taxes & fees
21 Jun - 22 Jun
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

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 992
AED 1,915 total
includes taxes & fees
22 Jun - 23 Jun
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 AED 793
AED 3,106 total
includes taxes & fees
22 Jun - 23 Jun
Fox Hollow at Carter Bridge Estate

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

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)
The price is AED 970
AED 1,519 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

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

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (5 reviews)
"House had everything, very clean, host very responsive, located close to everything. Great family vacation!"
United States
Jaylyn B.
The price is AED 993
AED 3,000 total
includes taxes & fees
22 Jun - 23 Jun
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

Modern Family Retreat in the Catskills Wilderness

Modern Family Retreat in the Catskills Wilderness
Round Top
Modern Family Retreat in the Catskills Wilderness

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 771
AED 2,039 total
includes taxes & fees
19 Jul - 20 Jul
Pines Vignette • Modern 3BR Home in Windham

Close to skiing and hiking, walk to main street

Close to skiing and hiking, walk to main street
Tannersville
9.2 out of 10, Wonderful, (15 reviews)
"We had a great time staying at the property. Location is really nice, close to the mountains. Checkin was smooth and host was accommodating to some of our requests."
United States
Rushabh V.
The price is AED 562
AED 1,579 total
includes taxes & fees
23 Jun - 24 Jun
Close to skiing and hiking, walk to main street

Pet friendly mountain house, stunning views, chefs kitchen, mins to Hunter/Windm

Pet friendly mountain house, stunning views, chefs kitchen, mins to Hunter/Windm
Maplecrest
4.0 out of 10, (2 reviews)
"- The house had a bud infestation and there were bugs flying around and dead on the floor- The number provided in case of emergencies was not active and went right to voicemail- The host was unresponsive for hours - There were 2 issues with the water1. It turned off and required to a trip to the basement for the circuit breaker. This was not communicated until the following morning at 5am2. The breaker for the hot water turned off and we had no hot water in the house- Outlets in the kitchen did...
United States
Liza B.
Pet friendly mountain house, stunning views, chefs kitchen, mins to Hunter/Windm
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