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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
The price is AED 275
AED 464 total
includes taxes & fees
15 Nov - 16 Nov
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, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is AED 404
AED 686 total
includes taxes & fees
16 Nov - 17 Nov
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 AED 1,157
AED 1,773 total
includes taxes & fees
16 Nov - 17 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A deck with a fire pit, outdoor seating, and a view of the landscape.

4. 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 AED 997
AED 1,851 total
includes taxes & fees
29 Nov - 30 Nov
Romantic Catskill Getaway | HotTub w/Mountain View
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
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AED 683
AED 1,849 total
includes taxes & fees
16 Nov - 17 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

6. Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.8 out of 10, Exceptional, (11 reviews)
"Secluded yet convenient. Homey. Quaint. Loved it! Will stay again!"
United States
Amber C.
The price is AED 441
AED 1,000 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Cabin-Catskills secluded Mountain retreat
A living room with a brick fireplace, leather sofa, and a flat-screen TV.

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

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
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 AED 1,228
AED 1,454 total
includes taxes & fees
26 Nov - 27 Nov
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
A cozy living room with wooden walls, a stone fireplace, and a television.

8. 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 AED 1,428
AED 2,320 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A spacious dining area with a high ceiling, exposed wooden beams, and hanging light fixtures.

9. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is AED 1,507
AED 2,871 total
includes taxes & fees
15 Nov - 16 Nov
Catskills Escape w/ Hot Tub & Fireplace
A spacious log cabin interior with a high ceiling, wooden floors, a billiards table, and a cozy seating area.

10. Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
The price is AED 8,264
AED 11,841 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
A cozy outdoor seating area with Adirondack chairs, a fire pit, and a stone fireplace.

11. **Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski

**Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski
Prattsville
9.4 out of 10, Exceptional, (10 reviews)
"The House is beautiful and nicely decorated. the kitchen is fully equipped, great back yard and many games in the game room, the jacuzzi was a great plus and we all gather around the fire pit. We loved the place amazing location and we will be happy to return back again."
United States
Hermine H.
The price is AED 3,434
AED 5,294 total
includes taxes & fees
23 Nov - 24 Nov
**Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski
Front of property

12. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (4 reviews)
"The best "
United States
Miguel
The price is AED 1,576
AED 1,992 total
includes taxes & fees
16 Nov - 17 Nov
Windham NY Escape
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

13. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (16 reviews)
"Location is great"
United States
Jennifer M.
The price is AED 1,745
AED 2,777 total
includes taxes & fees
14 Nov - 15 Nov
Condo in Windham Mountain Village
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.

14. 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 AED 604
AED 2,187 total
includes taxes & fees
16 Nov - 17 Nov
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

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

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (23 reviews)
"Great little cabin with nice atmosphere. It was an awesome place to spend the weekend and enjoy the Catskills. Clean, cozy, and quiet. A nice place to come back to and relax day after day."
United States
Andrea S.
The price is AED 325
AED 669 total
includes taxes & fees
15 Nov - 16 Nov
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Dining

16. Lux Mansion, Windham: Hot Tub, Sauna

Lux Mansion, Windham: Hot Tub, Sauna
Windham
10.0 out of 10, Exceptional, (4 reviews)
"The house was exactly as pictured and described. Beautiful home on a huge lot. "
United States
Whit M.
The price is AED 4,095
AED 7,236 total
includes taxes & fees
16 Nov - 17 Nov
Lux Mansion, Windham: Hot Tub, Sauna
A house with a fire pit and outdoor seating.

17. 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 price is AED 871
AED 2,714 total
includes taxes & fees
16 Nov - 17 Nov
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

18. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is AED 841
AED 1,548 total
includes taxes & fees
15 Nov - 16 Nov
Midnight Fox
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

19. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is AED 533
AED 597 total
includes taxes & fees
16 Nov - 17 Nov
Starlite Motel
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

20. Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
Windham
7.8 out of 10, Good, (6 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 AED 986
AED 1,220 total
includes taxes & fees
17 Nov - 18 Nov
Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
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
"Very clean, quiet AC, nice staff. Convenient location, easy to drive to nearby towns and hiking trails. À simple breakfast is included; good coffee all day. Quality of bedding and bath towels can be improved, but good enough for the price I paid."
Tianyu 3-night trip
Posted 4 hours ago
Hotel Vienna

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.