Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Ashland vacation rentals

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

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
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
Smart TV, fireplace, table tennis, video library
Stunning Catskills Cabin Getaway, facing BelleAyre

Stunning Catskills Cabin Getaway, facing BelleAyre

Stunning Catskills Cabin Getaway, facing BelleAyre
Fleischmanns
10.0 out of 10, Exceptional, (131)
"Absolutely fabulous place we stayed for my daughter’s wedding. "
United States
Robert Joseph J.
Stunning Catskills Cabin Getaway, facing BelleAyre
Smart TV, fireplace, DVD player, foosball
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
West Kill
9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
Smart TV, fireplace, books, stereo
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Fleischmanns
9.6 out of 10, Exceptional, (64)
"Nice place. Enjoyed the hot tub. Good restaurant down the road. Just what we needed. "
United States
john C.
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Smart TV, fireplace
A world where time stands still, close to Belleayre Ski & Wedding venues.

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
9.4 out of 10, Exceptional, (31)
"Beautiful house, clean and in a beautiful location. A perfect home for rest and enjoyment in nature"
United States
Janko S.
The price is ￥18,799
￥72,163 total
includes taxes & fees
Dec 15 - Dec 16
A world where time stands still, close to Belleayre Ski & Wedding venues.
Exterior
Beautiful new house 3/4 mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain
hunter
9.6 out of 10, Exceptional, (138)
"Really beautiful location with plenty of bedrooms. Very clean!"
United States
Ellen B.
Beautiful new house 3/4 mile from Hunter Mountain
Terrace/patio
Casa Rotunda: A Cozy Catskills Escape

Casa Rotunda: A Cozy Catskills Escape

Casa Rotunda: A Cozy Catskills Escape
2.0 star property
Margaretville
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this house for our anniversary weekend. My husband and I absolutely loved our time therе! The place is incredibly cozy, beautifully maintained, and offers a gorgeous view. The hot tub deserves a special mention: it’s amazing, very spacious, and would be perfect even for a larger group. We truly enjoyed every moment and highly recommend this home to anyone looking for a relaxing and memorable getaway"
United States
Mariia S.
Casa Rotunda: A Cozy Catskills Escape
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Hunter
10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
The price is ￥62,324
￥151,952 total
includes taxes & fees
Dec 15 - Dec 16
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Outdoor dining
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat
Windham
9.8 out of 10, Exceptional, (31)
"Excellent! The host was super friendly, helpful and was an excellent communicator. We had a great time!"
United States
Ray L.
A'Neils Windham Ski Lodge & Family Retreat
Terrace/patio
Private Waterfront on 6 Acres w/Hot Tub.Fire Pit.Views. Hiking.Games.

Private Waterfront on 6 Acres w/Hot Tub.Fire Pit.Views. Hiking.Games.

Private Waterfront on 6 Acres w/Hot Tub.Fire Pit.Views. Hiking.Games.
Prattsville
9.8 out of 10, Exceptional, (87)
"Lovely cozy spot with plenty to do inside and out. "
United States
Zachary W.
Private Waterfront on 6 Acres w/Hot Tub.Fire Pit.Views. Hiking.Games.
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains
Chichester
9.8 out of 10, Exceptional, (189)
"Nice place"
United States
Ron G.
The Cabin at Chichester in the Catskills Mountains
Exterior
Catskills Victorian With Fireplace & Mountain Views for skiing, fishing & hiking

Catskills Victorian With Fireplace & Mountain Views for skiing, fishing & hiking

Catskills Victorian With Fireplace & Mountain Views for skiing, fishing & hiking
Fleischmanns
9.6 out of 10, Exceptional, (89)
"The place is clean and roomy, stocked up with everything you need in great neighborhood next door to all year round activities. Would definitely rent again."
United States
Alex C.
Catskills Victorian With Fireplace & Mountain Views for skiing, fishing & hiking
Exterior
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Hunter
9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Exterior
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
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 ￥13,322
￥22,801 total
includes taxes & fees
Dec 14 - Dec 15
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior detail
Mountain Top Retreat, 116 private acres

Mountain Top Retreat, 116 private acres

Mountain Top Retreat, 116 private acres
Hobart
9.6 out of 10, Exceptional, (99)
"A mountain getaway of pure tranquility "
United States
Mike V.
Mountain Top Retreat, 116 private acres
Outdoor dining
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Windham
10.0 out of 10, Exceptional, (105)
"Rick has an incredible property to share and is a gracious host. A sure place to spend time with friends and family - cant wait to come back again."
United States
Chris R.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Exterior
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills
2.0 star property
Windham
10.0 out of 10, Exceptional, (12)
"Nice cozy home"
United States
Romonia F.
Magical Home Located in Windham and Catskills
Suite, 2 Bedrooms | Living area | TV
Suites on Main

Suites on Main

Suites on Main
3.0 star property
Margaretville
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
Smart TV, fireplace
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
Hunter Highlands
10.0 out of 10, Exceptional, (10)
"We loved staying at this condo. The location was amazing for back and forth to the slopes it was so easy! The beds were so comfortable and the house was clean! Communication with the owner was excellent. We will definitely stay again! "
United States
Melissa B.
The price is ￥125,669
￥203,032 total
includes taxes & fees
Dec 15 - Dec 16
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
4 bedrooms, desk, iron/ironing board, travel crib
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Hunter
9.6 out of 10, Exceptional, (31)
"Great stay in a great location. Mountain View with the fire pit was amazing! "
United States
Conor D.
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
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.