Search Vacation Homes in Ashland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Vacation Homes in Ashland

Exterior
Perfect 3-bedroom house at Tannersville

Perfect 3-bedroom house at Tannersville

2.0 star property
Tannersville
The price is AED 1,568
AED 2,614 total
includes taxes & fees
20 Nov - 21 Nov
Perfect 3-bedroom house at Tannersville
Fridge, microwave, oven, stovetop
Cozy Waterfall Home | Close to All Mountains/Hikes

Cozy Waterfall Home | Close to All Mountains/Hikes

3.0 star property
East Durham
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.
The price is AED 424
AED 1,188 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Waterfall Home | Close to All Mountains/Hikes
Property grounds
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
8.8 out of 10, Excellent, (53)
"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.
The price is AED 364
AED 678 total
includes taxes & fees
20 Nov - 21 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Terrace/patio
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

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

4.0 star property
Durham
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.
The price is AED 628
AED 1,702 total
includes taxes & fees
2 Dec - 3 Dec
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Exterior
The Homestead at Carter Bridge Estate

The Homestead at Carter Bridge Estate

Freehold
10.0 out of 10, Exceptional, (2)
"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
The price is AED 615
AED 2,049 total
includes taxes & fees
20 Nov - 21 Nov
The Homestead at Carter Bridge Estate
Exterior
Cozy Home, Wood-burning Fireplace, Ski Belleayre

Cozy Home, Wood-burning Fireplace, Ski Belleayre

Margaretville
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.
The price is AED 375
AED 1,265 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Home, Wood-burning Fireplace, Ski Belleayre
Fridge, microwave, oven, stovetop
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)
"Very clean and comfortable for the five of us. Close to windham and all of its activities"
United States
Jonathan M.
The price is AED 512
AED 1,160 total
includes taxes & fees
20 Nov - 21 Nov
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Smart TV, fireplace
Striped Bass Lodge at Carter Bridge Estate

Striped Bass Lodge at Carter Bridge Estate

Freehold
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.
The price is AED 694
AED 2,253 total
includes taxes & fees
20 Nov - 21 Nov
Striped Bass Lodge at Carter Bridge Estate
Exterior
Unwind Windham, Chalet

Unwind Windham, Chalet

Windham
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.
The price is AED 831
AED 2,290 total
includes taxes & fees
7 Dec - 8 Dec
Unwind Windham, Chalet
Private kitchen
Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount

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

2.0 star property
Pine Hill
10.0 out of 10, Exceptional, (1)
"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 750
AED 1,642 total
includes taxes & fees
20 Nov - 21 Nov
Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount
Smart TV, fireplace
Fox Hollow at Carter Bridge Estate

Fox Hollow at Carter Bridge Estate

East Durham
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.
The price is AED 793
AED 2,408 total
includes taxes & fees
20 Nov - 21 Nov
Fox Hollow at Carter Bridge Estate
TV, fireplace
Midnight Fox

Midnight Fox

Hunter
10.0 out of 10, Exceptional, (7)
"We had a great time "
United States
israel R.
The price is AED 841
AED 1,586 total
includes taxes & fees
20 Nov - 21 Nov
Midnight Fox
Dining
Newly Renovated Ski House in Windham

Newly Renovated Ski House in Windham

Hensonville
10.0 out of 10, Exceptional, (5)
"We had a great time during our stay, the owner was super helpful and we had everything that we needed for a nice ski getaway!"
United States
Tomer M.
The price is AED 518
AED 1,527 total
includes taxes & fees
23 Nov - 24 Nov
Newly Renovated Ski House in Windham
Outdoor dining
Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills

Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills

Margaretville
10.0 out of 10, Exceptional, (1)
"Our stay was peaceful and restful. The grounds are absolutely perfect for that. "
United States
Paulina P.
Cozy A-Frame Cabin | Summer Vibes & Pondside Relaxation in the Catskills
Outdoor pool
Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool

Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool

Hunter
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.
The price is AED 673
AED 1,262 total
includes taxes & fees
20 Nov - 21 Nov
Gorgeous & Cozy Mountain View with Wood Stove! Ski / Hiking / Wi-Fi / Pool
Pool
Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre

Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre

Jefferson
10.0 out of 10, Exceptional, (3)
"Small and cozy as advertised, perfect for a couple and hope to get back soon"
United States
Sean S.
The price is AED 911
AED 1,890 total
includes taxes & fees
30 Nov - 1 Dec
Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre
Fridge, microwave, oven, stovetop
Alpine Four Season Lodge Belleayre NY Sleeps 22

Alpine Four Season Lodge Belleayre NY Sleeps 22

2.0 star property
Shandaken
The price is AED 9,520
AED 14,716 total
includes taxes & fees
24 Nov - 25 Nov
Alpine Four Season Lodge Belleayre NY Sleeps 22
Dining
Luxury Mountain Villa- game room, hot-tub, firepit

Luxury Mountain Villa- game room, hot-tub, firepit

2.0 star property
Hunter
The price is AED 413
AED 2,144 total
includes taxes & fees
20 Nov - 21 Nov
Luxury Mountain Villa- game room, hot-tub, firepit
Interior
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham
The price is AED 526
AED 1,703 total
includes taxes & fees
1 Dec - 2 Dec
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Interior
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

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

2.0 star property
Phoenicia
9.0 out of 10, Wonderful, (28)
"The furnishings were cute and quaint. The beds were very comfy."
United States
Jan
The price is AED 591
AED 1,250 total
includes taxes & fees
20 Nov - 21 Nov
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

The Colonial Motel

The Colonial Motel

10/10 Excellent
"yes thank you"
John 2-night trip
Posted 2 days ago
The Colonial Motel