Ashland Vacation Rentals

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Check prices for these dates

Tonight
Dec 13 - Dec 14
Tomorrow
Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Ashland vacation rentals

Premium House, Kitchen, Mountain View | Private kitchen | Full-size fridge, microwave, coffee/tea maker
Starlite Motel

Aparthotel in Big Indian

Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (274)
"Awesome place to stay!"
United States
Earl
The price is ￥19,203
￥21,507 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Starlite Motel
Bar (on property)
Jessie's Harvest House Suite

Chalet in Tannersville

Jessie's Harvest House Suite
10.0 out of 10, Exceptional, (2)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is ￥14,616
￥26,918 total
includes taxes & fees
Dec 15 - Dec 16
Jessie's Harvest House Suite
Dining
Cozy Cabin-Catskills secluded Mountain retreat

Cabin in Gilboa

Cozy Cabin-Catskills secluded Mountain retreat
2.0 star property
10.0 out of 10, Exceptional, (2)
"Small cabin in the woods, nicely appointed and clean. 20 minute drive to Windham for shopping and dining. Cabin secluded and quiet, very peaceful spot."
United States
Lili
The price is ￥18,348
￥44,234 total
includes taxes & fees
Dec 17 - Dec 18
Cozy Cabin-Catskills secluded Mountain retreat
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.
The price is ￥17,984
￥50,386 total
includes taxes & fees
Dec 16 - Dec 17
Cozy Waterfall Home | Close to All Mountains/Hikes
Suite, 2 Bedrooms | Living area | TV
Suites on Main

Apartment in Margaretville

Suites on Main
3.0 star property
7.2 out of 10, Good, (78)
"Good place to stay and reasonable "
Canada
Marney
The price is ￥15,254
￥22,686 total
includes taxes & fees
Dec 14 - Dec 15
Suites on Main
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.
The price is ￥15,902
￥53,998 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Home, Wood-burning Fireplace, Ski Belleayre
Outdoor spa tub
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Cottage in Phoenicia

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
9.8 out of 10, Exceptional, (23)
"Had a wonderful "
United States
Alexandra R.
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
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.
The price is ￥26,644
￥71,854 total
includes taxes & fees
Dec 14 - Dec 15
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Smart TV, fireplace
Relaxing Mountain Hideaway - Hot Tub & Outdoors

Chalet in Hensonville

Relaxing Mountain Hideaway - Hot Tub & Outdoors
2.0 star property
The price is ￥17,143
￥110,875 total
includes taxes & fees
Dec 15 - Dec 16
Relaxing Mountain Hideaway - Hot Tub & Outdoors
Property grounds
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Cabin in Palenville

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
10.0 out of 10, Exceptional, (29)
"Very clean, beautiful property! Would highly recommend staying here, and we will be coming up again someday. The host provided everything and was very diligent on the details that make this a wonderful and unique place to stay"
United States
Nick A.
The price is ￥31,552
￥56,457 total
includes taxes & fees
Dec 14 - Dec 15
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Smart TV, books
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Apartment in Phoenicia

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby
10.0 out of 10, Exceptional, (26)
"Very relaxing stay in a beautiful place! The hosts are considerate and a pleasure to deal with. Highly recommend for a rejuvenating getaway."
United States
daniel d.
The price is ￥19,772
￥25,637 total
includes taxes & fees
Dec 16 - Dec 17
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby
Interior
Spacious Catskill Mountains ski cabin with fire pit

Cabin in Maplecrest

Spacious Catskill Mountains ski cabin with fire pit
9.8 out of 10, Exceptional, (19)
"The house was exactly what we were looking for! Close to the ski mountains, town and made for a really nice weekend away!"
United States
Lauren P.
The price is ￥27,906
￥61,436 total
includes taxes & fees
Dec 14 - Dec 15
Spacious Catskill Mountains ski cabin with fire pit
Exterior
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Apartment in Windham

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥13,294
￥22,754 total
includes taxes & fees
Dec 18 - Dec 19
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Property grounds
Cold Spring Lodge - Cabin 2

Cabin in Big Indian

Cold Spring Lodge - Cabin 2
9.6 out of 10, Exceptional, (4)
"We had a nice relaxing stay"
United States
Michael
The price is ￥22,086
￥37,824 total
includes taxes & fees
Dec 14 - Dec 15
Cold Spring Lodge - Cabin 2
Dining
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Cabin in Lanesville

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
9.8 out of 10, Exceptional, (17)
"Simply perfect! This house was clean, fully stocked of all necessities and optimally located for hiking, town hoping, art seeing and brewery bouncing. Would love to come back in the winter for its proximity to Hunter Mountain. Highly recommend!"
United States
Sarah P.
The price is ￥30,429
￥78,600 total
includes taxes & fees
Dec 14 - Dec 15
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Pool
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Apartment in Hunter Highlands

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
9.8 out of 10, Exceptional, (7)
"Great stay! We will be back!"
United States
Michael
The price is ￥20,099
￥38,982 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
Bar (on property)
Jessie's Harvest House

Chalet in Tannersville

Jessie's Harvest House
The price is ￥18,348
￥31,453 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Jessie's Harvest House
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
The price is ￥49,136
￥132,155 total
includes taxes & fees
Dec 30 - Dec 31
The Homestead at Carter Bridge Estate
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.
The price is ￥21,691
￥49,623 total
includes taxes & fees
Dec 17 - Dec 18
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
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.
The price is ￥22,391
￥36,945 total
includes taxes & fees
Dec 18 - Dec 19
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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

Black Bear Lodge

Black Bear Lodge

10/10 Excellent
"Easy parking, pet friendly, this property is clean and comfortable. The location is scenic and rural."
Kathleen 2-night trip
Posted 2 days ago
Black Bear Lodge

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

  • View our selection of featured holiday rentals in Ashland
  • Use the map to find apartments and other holiday homes in the Ashland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

Look no further and take a look at our great range of rental properties in Ashland!

Frequently asked questions

Can I find a vacation rental in Ashland?

Yes, we offer vacation rentals near popular attractions in Ashland, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Ashland has to offer?

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing : This vacation home rental near Ashland is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Ashland?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Ashland stay.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Hobart Book Village, or get outside and enjoy nature at Mountain Top Arboretum. Ashland Town Hall and Hunter Mountain are a couple of places you'll find in the larger area.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can book for several days or longer in Ashland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.