Search Vacation Homes in Ashland

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Ashland vacation homes

Interior
Cozy Waterfall Home | Close to All Mountains/Hikes

Vacation Home in East Durham

Cozy Waterfall Home | Close to All Mountains/Hikes
3.0 star property
10.0 out of 10, Exceptional, (3)
"The host is very responsive and the listing is accurate about what to expect with the property."
United States
John K.
$299 nightly
The price is $323
Dec 14 - Dec 15
Total with taxes and fees
Cozy Waterfall Home | Close to All Mountains/Hikes
Outdoor dining
Cozy Home, Wood-burning Fireplace, Ski Belleayre

Vacation Home in Margaretville

Cozy Home, Wood-burning Fireplace, Ski Belleayre
9.8 out of 10, Exceptional, (10)
"Dunraven River House was perfect for our weekend away. The house was clean, comfortable and exactly as listed. The property so was peaceful and I loved having the sounds of the river right outside the door! We’d definitely stay again! "
United States
Angela P.
$310 nightly
The price is $341
Dec 15 - Dec 16
Total with taxes and fees
Cozy Home, Wood-burning Fireplace, Ski Belleayre
Interior
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Vacation Home in Durham

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
4.0 star property
10.0 out of 10, Exceptional, (2)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
$437 nightly
The price is $472
Dec 14 - Dec 15
Total with taxes and fees
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Property grounds
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Vacation Home in Hensonville

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
10.0 out of 10, Exceptional, (10)
"Very clean and comfortable for the five of us. Close to windham and all of its activities"
United States
Jonathan M.
$285 nightly
The price is $307
Dec 15 - Dec 16
Total with taxes and fees
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Outdoor dining
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Vacation Home in Windham

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
2.5 star property
$970 nightly
The price is $1,048
Dec 26 - Dec 27
Total with taxes and fees
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Interior
The Homestead at Carter Bridge Estate

Vacation Home in Freehold

The Homestead at Carter Bridge Estate
10.0 out of 10, Exceptional, (3)
"This was an excellent home that we stayed in total of six adults. We went to the Gray Fox music festival and it was very close by. The property manager was very responsive and communicative. Highly recommend this house."
United States
ELIZABETH
$628 nightly
The price is $679
Dec 14 - Dec 15
Total with taxes and fees
The Homestead at Carter Bridge Estate
Exterior
Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite

Vacation Home in Halcott Center

Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite
2.0 star property
$395 nightly
The price is $427
Dec 12 - Dec 13
Total with taxes and fees
Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite
Exterior
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Vacation Home in Windham

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
9.0 out of 10, Wonderful, (54)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
$220 nightly
The price is $238
Dec 14 - Dec 15
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Sauna
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

Vacation Home in Phoenicia

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
2.0 star property
9.2 out of 10, Wonderful, (31)
"The furnishings were cute and quaint. The beds were very comfy."
United States
Jan
$310 nightly
The price is $347
Dec 14 - Dec 15
Total with taxes and fees
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Smart TV, fireplace
A world where time stands still, close to Belleayre Ski & Wedding venues.

Vacation Home in City Roxbury

A world where time stands still, close to Belleayre Ski & Wedding venues.
9.4 out of 10, Exceptional, (30)
"Beautiful house, clean and in a beautiful location. A perfect home for rest and enjoyment in nature"
United States
Janko S.
$417 nightly
The price is $459
Dec 15 - Dec 16
Total with taxes and fees
A world where time stands still, close to Belleayre Ski & Wedding venues.
Smart TV, fireplace
Fox Hollow at Carter Bridge Estate

Vacation Home in East Durham

Fox Hollow at Carter Bridge Estate
10.0 out of 10, Exceptional, (2)
"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.
$740 nightly
The price is $799
Dec 14 - Dec 15
Total with taxes and fees
Fox Hollow at Carter Bridge Estate
Outdoor spa tub
Striped Bass Lodge at Carter Bridge Estate

Vacation Home in Freehold

Striped Bass Lodge at Carter Bridge Estate
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay, very clean, beds were very comfortable, property manager was very quick to respond. Recommend asking for WiFi access code prior to arrival. "
United States
Susanne T.
$709 nightly
The price is $766
Dec 14 - Dec 15
Total with taxes and fees
Striped Bass Lodge at Carter Bridge Estate
Terrace/patio
Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills

Vacation Home in Margaretville

Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills
10.0 out of 10, Exceptional, (1)
"Our stay was peaceful and restful. The grounds are absolutely perfect for that. "
United States
Paulina P.
$427 nightly
The price is $472
Dec 15 - Dec 16
Total with taxes and fees
Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills
Interior
Cute Cozy Catskill Escape

Vacation Home in Tannersville

Cute Cozy Catskill Escape
10.0 out of 10, Exceptional, (1)
"This was the most stunning relaxing weekend me and my family had for years. clean and beautiful cozy house beautiful neighbourhood and some nice attractions in the area and most of all the best host you can ever hope for, from making sure everything is alright being responsive right away and what not he had no problem with anything we asked for. It’s a well maintained house and a brand new fridge freezer grill dishwasher dishes everything just perfect so if you are looking for a wonderful time...
United States
Benjamin S.
$517 nightly
The price is $558
Dec 14 - Dec 15
Total with taxes and fees
Cute Cozy Catskill Escape
Fridge, microwave, oven, stovetop
Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool

Vacation Home in Hunter

Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool
9.4 out of 10, Exceptional, (3)
"My partner and I planned a small getaway to Hunter mountain for a day of skiing and snow hiking. This sweet apartment was only a few minutes away from the mountain and welcomed us with a warm, clean, spacious, and mountain themed atmosphere. 10/10 would recommend!"
United States
Gabrielle M.
$321 nightly
The price is $347
Dec 14 - Dec 15
Total with taxes and fees
Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool
Dining
2 Min Walk to Windham Town | Hot Tub | Fire Pit

Vacation Home in Windham

2 Min Walk to Windham Town | Hot Tub | Fire Pit
10.0 out of 10, Exceptional, (1)
"It was amazing for a big family! Tons of space, and everything was very clean! The hosts were also very pleasant to deal with."
United States
Hadassah S.
$452 nightly
The price is $488
Dec 15 - Dec 16
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Dining
Unwind Windham, Chalet

Vacation Home in Windham

Unwind Windham, Chalet
10.0 out of 10, Exceptional, (2)
"We stayed only one night and we thought that should stay more nights because of the comfort of the house, the location, the amenities and the Property Host was there for answer any question. Definitely we come back now with the conviction that we have everything we need for an escape from New York city. I recommend this place in a 100% for sure. "
United States
Karla R.
$834 nightly
The price is $842
Dec 12 - Dec 13
Total with taxes and fees
Unwind Windham, Chalet
Interior
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Vacation Home in Tannersville

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
10.0 out of 10, Exceptional, (2)
"Great time had by all of us! House is perfect for several families and so much to do in the area. Would definitely stay again! Owners were very easy to access for questions."
United States
Michelle D.
$619 nightly
The price is $669
Dec 16 - Dec 17
Total with taxes and fees
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Interior
2-bedroom in Peaceful Middleburgh Vroman’s Nose View

Vacation Home in Middleburgh

2-bedroom in Peaceful Middleburgh Vroman’s Nose View
2.5 star property
$213 nightly
The price is $239
Dec 14 - Dec 15
Total with taxes and fees
2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Exterior
Cozy Country Farmhouse Along the Catskill Scenic Trail

Vacation Home in Hobart

Cozy Country Farmhouse Along the Catskill Scenic Trail
10.0 out of 10, Exceptional, (127)
"We stay here year after year! It is always clean, quiet, and well stocked. It feels like home away from home. "
United States
Andrea P.
$291 nightly
The price is $320
Dec 18 - Dec 19
Total with taxes and fees
Cozy Country Farmhouse Along the Catskill Scenic Trail
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas!"
Bruce 1-night trip
Posted 2 days ago
Hotel Vienna

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
242
Accommodation
543 Vacation Homes
Lowest Price
$238
Highest Price
$842

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