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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Ashland vacation rentals

Exterior

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 AED 312
AED 536 total
includes taxes & fees
14 Sep - 15 Sep
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

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
9.0 out of 10, Wonderful, (63 reviews)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
The price is AED 588
AED 940 total
includes taxes & fees
7 Sep - 8 Sep
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Dining

3. 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 AED 441
AED 1,008 total
includes taxes & fees
10 Sep - 11 Sep
Cozy Cabin-Catskills secluded Mountain retreat
Premium House, Kitchen, Mountain View | Private kitchen | Coffee/tea maker, full-size fridge, microwave

4. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (313 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
The price is AED 459
AED 514 total
includes taxes & fees
8 Sep - 9 Sep
Starlite Motel
Property grounds

5. Romantic Catskill Getaway | HotTub w/Mountain View

Romantic Catskill Getaway | HotTub w/Mountain View
Prattsville
10.0 out of 10, Exceptional, (3 reviews)
"Really beautiful place"
United States
Ramsey
The price is AED 836
AED 1,694 total
includes taxes & fees
9 Sep - 10 Sep
Romantic Catskill Getaway | HotTub w/Mountain View
Exterior

6. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (31 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is AED 477
AED 817 total
includes taxes & fees
8 Sep - 9 Sep
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
TV, fireplace

7. 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 AED 661
AED 1,856 total
includes taxes & fees
9 Sep - 10 Sep
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Property grounds

8. Cozy Mountain Dome Escape in the Catskills

Cozy Mountain Dome Escape in the Catskills
Gilboa
10.0 out of 10, Exceptional, (4 reviews)
"We were camping with our entire family of 4 boys and their significant others and children. We stayed in the Dome for the nights creating space for the camper free family and it was lovely!"
United States
kim h.
The price is AED 405
AED 680 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Mountain Dome Escape in the Catskills
Coffee/tea maker, fridge, microwave, oven

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

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (19 reviews)
"Perfect little cabin for our Thanksgiving getaway! "
United States
Gabrielle G.
The price is AED 347
AED 733 total
includes taxes & fees
13 Sep - 14 Sep
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Interior

10. 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 AED 606
AED 1,634 total
includes taxes & fees
8 Sep - 9 Sep
West Kill Barnhouse: Ski, Work & Unwind
Front of property

11. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
The price is AED 1,576
AED 1,992 total
includes taxes & fees
10 Sep - 11 Sep
Windham NY Escape
Dining

12. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is AED 735
AED 1,952 total
includes taxes & fees
8 Sep - 9 Sep
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Property grounds

13. 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 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 AED 661
AED 1,345 total
includes taxes & fees
8 Sep - 9 Sep
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Coffee/tea maker, fridge, microwave, oven

14. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
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 575
AED 737 total
includes taxes & fees
7 Sep - 8 Sep
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Property grounds

15. Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is AED 574
AED 741 total
includes taxes & fees
8 Sep - 9 Sep
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Interior

16. 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 1,627 total
includes taxes & fees
9 Sep - 10 Sep
Midnight Fox
Exterior

17. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is AED 790
AED 2,035 total
includes taxes & fees
30 Sep - 1 Oct
Pines Vignette • Modern 3BR Home in Windham
In-room safe, bed sheets

18. MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
Windham
8.0 out of 10, Very Good, (4 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 731
AED 940 total
includes taxes & fees
7 Sep - 8 Sep
MIRROR CABIN IN THE FOREST WITH HOT TUB
Interior

19. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.4 out of 10, Exceptional, (30 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is AED 658
AED 1,472 total
includes taxes & fees
6 Sep - 7 Sep
Spacious Catskill Mountains ski cabin with fire pit
Property grounds

20. 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 875
AED 2,869 total
includes taxes & fees
6 Sep - 7 Sep
Relaxing Mountain Hideaway - Hot Tub & Outdoors
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
"Nice small hotel for weekend getaway. Croissants for breakfast."
Harry 2-night trip
Posted 16 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?

Swim. Float. Fish. on private waterfront w/Hot Tub.Fire Pit.Views. Hiking.Games.: This vacation home rental near Ashland is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a patio, 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 4 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 Belleayre Beach. Ashland Town Hall and Windham Mountain Resort 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.