Default HTG hotel image

Ashland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

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.
$135 nightly
The price is $146
Sep 14 - Sep 15
Total with taxes and fees
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
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
$237 nightly
The price is $256
Sep 7 - Sep 8
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

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
$245 nightly
The price is $274
Sep 10 - Sep 11
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.

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
$125 nightly
The price is $140
Sep 8 - Sep 9
Total with taxes and fees
Starlite Motel
A deck with a fire pit, outdoor seating, and a view of the landscape.

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
$415 nightly
The price is $448
Sep 10 - Sep 11
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
A log cabin with a porch, a staircase, and a garage.

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.
$206 nightly
The price is $222
Sep 8 - Sep 9
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
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.
$468 nightly
The price is $505
Sep 9 - Sep 10
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A natural landscape with a lake, rocky cliffs, and a bench.

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.
$160 nightly
The price is $179
Sep 9 - Sep 10
Total with taxes and fees
Cozy Mountain Dome Escape in the Catskills
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

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.
$182 nightly
The price is $200
Sep 13 - Sep 14
Total with taxes and fees
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

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.
$394 nightly
The price is $425
Sep 9 - Sep 10
Total with taxes and fees
West Kill Barnhouse: Ski, Work & Unwind

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
$459 nightly
The price is $496
Sep 11 - Sep 12
Total with taxes and fees
Windham NY Escape
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

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.
$483 nightly
The price is $522
Sep 14 - Sep 15
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

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.
$339 nightly
The price is $366
Sep 8 - Sep 9
Total with taxes and fees
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A kitchen with green cabinets, a stainless steel stove, and a microwave.

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.
$176 nightly
The price is $201
Sep 7 - Sep 8
Total with taxes and fees
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

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
$179 nightly
The price is $201
Sep 8 - Sep 9
Total with taxes and fees
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

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.
$439 nightly
The price is $443
Sep 9 - Sep 10
Total with taxes and fees
Midnight Fox
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

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.
$534 nightly
The price is $577
Sep 14 - Sep 15
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

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.
$225 nightly
The price is $256
Sep 7 - Sep 8
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
A cozy cabin interior with a wooden interior, a spiral staircase, a kitchen area, and a seating area with a view.

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
$372 nightly
The price is $402
Sep 7 - Sep 8
Total with taxes and fees
Spacious Catskill Mountains ski cabin with fire pit
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.

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.
$736 nightly
The price is $795
Sep 7 - Sep 8
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

8/10 Good
"Clean , comfortable , did not use amenities bc we arrived too late . They had an indoors pool , a couple of places where you could make and sit by the fire and a corn hall . Breakfast was ok . Cereals, variety of coffees or tea . Various croissants and yougurt !"
Roxana 1-night trip
Posted 5 hours ago
Hotel Vienna

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?

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.