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Ashland Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$127 nightly
The price is $137
Sep 22 - Sep 23
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Premium House, Kitchen, Mountain View | Private kitchen | Coffee/tea maker, full-size fridge, microwave

2. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 22 - Sep 23
Total with taxes and fees
Starlite Motel
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
$254 nightly
The price is $284
Sep 22 - Sep 23
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
Exterior

4. 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, (64 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
$239 nightly
The price is $258
Sep 24 - Sep 25
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

5. 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, (33 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
$205 nightly
The price is $221
Sep 22 - Sep 23
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Property grounds

6. Peaceful Dome Getaway in the Catskills

Peaceful Dome Getaway in the Catskills
Gilboa
$155 nightly
The price is $173
Sep 23 - Sep 24
Total with taxes and fees
Peaceful Dome Getaway in the Catskills
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.
$466 nightly
The price is $503
Sep 23 - Sep 24
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Coffee/tea maker, fridge, microwave, oven

8. 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.
$178 nightly
The price is $196
Sep 27 - Sep 28
Total with taxes and fees
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Interior

9. 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.
$363 nightly
The price is $392
Oct 4 - Oct 5
Total with taxes and fees
West Kill Barnhouse: Ski, Work & Unwind
Dining

10. 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.
$478 nightly
The price is $516
Sep 23 - Sep 24
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Outdoor dining

11. Scribners Retreat | Sleeps 6 | Huge Patio/Jacuzzi

Scribners Retreat | Sleeps 6 | Huge Patio/Jacuzzi
Tannersville
$220 nightly
The price is $237
Sep 22 - Sep 23
Total with taxes and fees
Scribners Retreat | Sleeps 6 | Huge Patio/Jacuzzi
Property grounds

12. 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.
$339 nightly
The price is $366
Sep 22 - Sep 23
Total with taxes and fees
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Front of property

13. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
$502 nightly
The price is $542
Sep 22 - Sep 23
Total with taxes and fees
Windham NY Escape
In-room safe, bed sheets

14. 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.
$225 nightly
The price is $256
Sep 22 - Sep 23
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
Coffee/tea maker, fridge, microwave, oven

15. 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.
$178 nightly
The price is $203
Sep 23 - Sep 24
Total with taxes and fees
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Exterior

16. 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.
$496 nightly
The price is $536
Sep 22 - Sep 23
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
Interior

17. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.6 out of 10, Exceptional, (31 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
$371 nightly
The price is $401
Sep 22 - Sep 23
Total with taxes and fees
Spacious Catskill Mountains ski cabin with fire pit
Property grounds

18. 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
$546 nightly
The price is $588
Sep 29 - Sep 30
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
Property grounds

19. 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.
$723 nightly
The price is $780
Sep 22 - Sep 23
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors
TV, fireplace, video games, stereo

20. Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
Hunter Highlands
10.0 out of 10, Exceptional, (23 reviews)
"You will definitely return this place is cozy, clean and convenient! "
United States
Elizabeth C.
$214 nightly
The price is $233
Sep 22 - Sep 23
Total with taxes and fees
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

10/10 Excellent
"I have stayed at well over a dozen motels, hotels, lodges, resorts over my time in the Catskills. This was by far one of my favorites and is almost certainly going to become my regular resting spot. The location is premium, with it located in the heart of the Catskills, and not far from most attractions and hikes. The bar itself serves great food and drinks, and Sean and the staff are a delight to speak to. The room is clean, well maintained, and the cleaning staff do a great job each day. Most of the common motel flaws are virtually non-existent here. I could not hear my neighbors, they seemingly could not hear me, there were little to no stains on any bedding, the bathroom was spotless, and the ambience was unmatched. The biggest criticism I’ve heard from other people is that their rooms are outdated, and how anyone can stay the night and not fall in love with the rustic 70s charm is beyond me. Thanks for a great weekend, and I look forward to many more."
Asher 2-night trip
Posted 6 hours ago
Jimmy OConnors Windham Mountain Inn

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 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 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.