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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Ashland vacation rentals

A two-story building with large windows and a storefront.

1. 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, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is ￥11,852
￥21,333 total
includes taxes & fees
Nov 1 - Nov 2
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A two-story building with large windows and a storefront.

2. 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, (65 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is ￥17,382
￥30,890 total
includes taxes & fees
Nov 2 - Nov 3
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Entryway area

3. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is ￥55,307
￥87,208 total
includes taxes & fees
Oct 26 - Oct 27
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

4. Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.8 out of 10, Exceptional, (11 reviews)
"Great place to get away. "
United States
Joshua
The price is ￥18,962
￥43,714 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Cabin-Catskills secluded Mountain retreat
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥29,550
￥81,747 total
includes taxes & fees
Oct 21 - Oct 22
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A deck with a fire pit, outdoor seating, and a view of the landscape.

6. Romantic Catskill Getaway | HotTub w/Mountain View

Romantic Catskill Getaway | HotTub w/Mountain View
Prattsville
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay! The cabin was clean, cozy, and peaceful, surrounded by beautiful nature. It was the perfect place to relax and enjoy the tranquility. Thank you for your warm hospitality! We would love to come back again."
United States
Alena
The price is ￥49,192
￥89,925 total
includes taxes & fees
Nov 10 - Nov 11
Romantic Catskill Getaway | HotTub w/Mountain View
A kitchen with green cabinets, a stainless steel stove, and a microwave.

7. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is ￥26,381
￥34,132 total
includes taxes & fees
Oct 20 - Oct 21
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

8. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (320 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is ￥22,913
￥25,663 total
includes taxes & fees
Oct 20 - Oct 21
Starlite Motel
A log cabin with a porch, a staircase, and a garage.

9. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.2 out of 10, Wonderful, (35 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
The price is ￥20,543
￥35,157 total
includes taxes & fees
Oct 20 - Oct 21
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A picnic setup with a wine glass, bottle, cheese, tomatoes, and grapes on a wooden table with a view of a grassy field and hills.

10. Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors
Hensonville
10.0 out of 10, Exceptional, (3 reviews)
"Great house and great host! Very convenient location particularly to Windham Mountain. "
United States
Kyrill A.
The price is ￥22,733
￥108,345 total
includes taxes & fees
Nov 1 - Nov 2
Relaxing Mountain Hideaway - Hot Tub & Outdoors
Interior

11. Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!

Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
West Kill
10.0 out of 10, Exceptional, (2 reviews)
"If you've lived in an old house before, then you know what to expect. It was good for our needs during our short stay. The house is spacious and there is lots of light. The beds were comfortable and the water pressure was awesome. There is an a/c in every upstairs bedroom."
United States
Alexandra I.
Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
A wooden interior with a central fireplace, benches, and a window offering a forest view.

12. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Great stay highly recommend!"
United States
Shannon H.
The price is ￥56,887
￥101,031 total
includes taxes & fees
Nov 2 - Nov 3
Mountain house with Scandinavian BBQ hut and Hot tub
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

13. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is ￥21,491
￥64,681 total
includes taxes & fees
Oct 25 - Oct 26
West Kill Barnhouse: Ski, Work & Unwind
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

14. 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, (11 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 ￥28,444
￥58,196 total
includes taxes & fees
Oct 20 - Oct 21
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A cozy living room with wooden walls, a stone fireplace, and a television.

15. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
The price is ￥62,291
￥104,821 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

16. Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (1 review)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
The price is ￥16,128
￥30,451 total
includes taxes & fees
Nov 3 - Nov 4
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

17. Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain

Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
Windham
7.6 out of 10, Good, (5 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
The price is ￥33,816
￥43,670 total
includes taxes & fees
Oct 26 - Oct 27
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
A wooden cabin with a porch, two chairs, and a table.

18. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Halcott Center
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect during my stay. The service was excellent, and everything went very smoothly. I’m really happy with the overall experience and would highly recommend it to anyone."
United States
Hnin
The price is ￥18,773
￥68,059 total
includes taxes & fees
Nov 8 - Nov 9
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

19. Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (22 reviews)
"Perfect little cabin for our Thanksgiving getaway! "
United States
Gabrielle G.
The price is ￥19,199
￥36,241 total
includes taxes & fees
Nov 1 - Nov 2
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
A house with a fire pit and outdoor seating.

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

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic property. Especially good for families or groups. So much to do right on property, almost no need to leave. Place was exactly as described."
United States
David H.
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
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

Emerson Resort & Spa

Emerson Resort & Spa

10/10 Excellent
"The Emmerson Resort & Spa is great! The room was super clean and the bed was very comfortable. The resort is great and has everything you need. We loved staying here!"
Jeremy 2-night trip
Posted 2 hours ago
Emerson Resort & Spa

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:

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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?

Heart of Hunter Village; across MT!FALL Special3rd nt half OFF!”wknd stay: 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 6 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, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Ashland?

With 3 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 Zoom Flume, or get outside and enjoy nature at Mountain Top Arboretum. Ashland Town Hall and Windham Vineyards and Winery 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.