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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Ashland vacation rentals

Entryway area

1. 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.
$468 nightly
The price is $505
Oct 13 - Oct 14
Total with taxes and fees
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A spacious kitchen with a dining area, large windows, and a ceiling fan.

2. Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies

Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
Prattsville
9.6 out of 10, Exceptional, (9 reviews)
"The cabin was charming, the kitchen was stocked with tools for cooking, and the wood fired hot tub was magical. It's a perfect place for families or a couple who are looking for a Catskills getaway or are skiing in the area. Would definitely come back."
United States
Bengt A.
$558 nightly
The price is $563
Oct 13 - Oct 14
Total with taxes and fees
Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
A deck with a fire pit, outdoor seating, and a view of the landscape.

3. 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
$507 nightly
The price is $546
Nov 10 - Nov 11
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
A two-story building with large windows and a storefront.

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
$216 nightly
The price is $233
Oct 18 - Oct 19
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A two-story building with large windows and a storefront.

5. 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.
$125 nightly
The price is $135
Nov 1 - Nov 2
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A wooden interior with a central fireplace, benches, and a window offering a forest view.

6. 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)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
$637 nightly
The price is $688
Nov 2 - Nov 3
Total with taxes and fees
Mountain house with Scandinavian BBQ hut and Hot tub
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

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.
$447 nightly
The price is $483
Nov 3 - Nov 4
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Front of property

8. 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
Oct 13 - Oct 14
Total with taxes and fees
Windham NY Escape
A cozy living room with wooden walls, a stone fireplace, and a television.

9. 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.
$658 nightly
The price is $711
Oct 19 - Oct 20
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A lodge with a hot tub, wooden exterior, and a covered deck.

10. Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace

Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
Lexington
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed a week here with our two daughters and their husbands. The chalet was fantastic, as was the scenery. highly recommend this location."
Canada
Steven K.
$785 nightly
The price is $848
Nov 8 - Nov 9
Total with taxes and fees
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
A bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a sink and mirror.

11. Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace

Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
Windham
$283 nightly
The price is $322
Nov 2 - Nov 3
Total with taxes and fees
Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

12. 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
Oct 13 - Oct 14
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

13. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (316 reviews)
"Everything was great"
United States
Danielle
$145 nightly
The price is $162
Oct 13 - Oct 14
Total with taxes and fees
Starlite Motel
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

14. 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.
$909 nightly
The price is $982
Oct 13 - Oct 14
Total with taxes and fees
Condo in Windham Mountain Village
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

15. 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.
$309 nightly
The price is $352
Nov 3 - Nov 4
Total with taxes and fees
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
Dining

16. Lux Mansion, Windham: Hot Tub, Sauna

Lux Mansion, Windham: Hot Tub, Sauna
Windham
10.0 out of 10, Exceptional, (4 reviews)
"It was a wonderful house. The first few days were very cold and it was spacious and there was a lot to do within the house and it was very comfortable to stay in! When it warmed up we were literally 5 minutes from the slopes and 3 minutes from the town."
United States
RoseMarie D.
$1,639 nightly
The price is $1,770
Oct 19 - Oct 20
Total with taxes and fees
Lux Mansion, Windham: Hot Tub, Sauna
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

17. 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.
$439 nightly
The price is $443
Oct 14 - Oct 15
Total with taxes and fees
Midnight Fox
A house with a fire pit and outdoor seating.

18. 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.
$660 nightly
The price is $713
Oct 20 - Oct 21
Total with taxes and fees
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A circular arrangement of Adirondack chairs around a central fire pit in a lush, green outdoor setting.

19. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$518 nightly
The price is $559
Oct 13 - Oct 14
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Interior

20. 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.
$483 nightly
The price is $521
Oct 13 - Oct 14
Total with taxes and fees
Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

8/10 Good
"I like this place very much. It is beautiful, clean and in a great location. The heated pool and jacuzzi, the fireplaces, all wonderful. But I think the studio room we had was VERY overpriced."
Donald R 2-night trip
Posted less than an hour ago
Kaatskill Mountain Club & Condos by Vail Resorts

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 $162 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 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.