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Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

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
Jul 22 - Jul 23
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.6 out of 10, Exceptional, (9 reviews)
$254 nightly
The price is $284
Aug 2 - Aug 3
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat

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, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
$205 nightly
The price is $221
Aug 3 - Aug 4
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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.
$578 nightly
The price is $625
Jul 26 - Jul 27
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (306 reviews)
"Perfect for us- so close to the mountain and kitchen was great "
United States
Elizabeth
$125 nightly
The price is $140
Jul 22 - Jul 23
Total with taxes and fees
Starlite Motel

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.2 out of 10, Wonderful, (27 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
$200 nightly
The price is $216
Jul 22 - Jul 23
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

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.
$326 nightly
The price is $352
Jul 22 - Jul 23
Total with taxes and fees
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Cozy Mountain Dome Escape in the Catskills

Cozy Mountain Dome Escape in the Catskills
Gilboa
10.0 out of 10, Exceptional, (4 reviews)
"Campground very clean and family friendly. Restrooms a very clean, water pressure for showers is decent water pressure but also depends upon how many people are actively at the campground using water right then. Was perfect for a nice little getaway. Strongly advice!!"
United States
Katrina Z.
$165 nightly
The price is $185
Jul 22 - Jul 23
Total with taxes and fees
Cozy Mountain Dome Escape in the Catskills

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
$410 nightly
The price is $442
Jul 30 - Jul 31
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!
Lanesville
10.0 out of 10, Exceptional, (3 reviews)
"Had a wonderful weekend getaway here. The property is just as described, awesome communication and recs, and VERY convenient to the mountain. Would highly recommend if you are looking to relax and unwind away from the crowds that the nearby hotels have. Very conveniently located to some great restaurants and cafes. Thoroughly enjoyed ourselves! "
United States
Krista F.
$219 nightly
The price is $238
Jul 22 - Jul 23
Total with taxes and fees
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!

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, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
$490 nightly
The price is $529
Jul 22 - Jul 23
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Cozy Downtown Hunter Mountain Getaway

Cozy Downtown Hunter Mountain Getaway
Lanesville
$143 nightly
The price is $154
Jul 22 - Jul 23
Total with taxes and fees
Cozy Downtown Hunter Mountain Getaway

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (17 reviews)
"Perfect little cabin for our Thanksgiving getaway! "
United States
Gabrielle G.
$186 nightly
The price is $205
Jul 23 - Jul 24
Total with taxes and fees
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

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, (22 reviews)
"Great experience "
United States
Harjeet K.
$226 nightly
The price is $246
Aug 5 - Aug 6
Total with taxes and fees
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!

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.
$531 nightly
The price is $573
Jul 29 - Jul 30
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns
Halcott Center
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect during my stay. The service was excellent, and everything went very smoothly. I’m really happy with the overall experience and would highly recommend it to anyone."
United States
Hnin
$426 nightly
The price is $460
Jul 29 - Jul 30
Total with taxes and fees
Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

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
Jul 23 - Jul 24
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham

Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
$165 nightly
The price is $174
Jul 22 - Jul 23
Total with taxes and fees
Jessie's Harvest House Suite

Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (2 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$211 nightly
The price is $224
Jul 23 - Jul 24
Total with taxes and fees
Jessie's Harvest House

Hunter Mountain 2 Bedroom Condo - Steps to Ski Slopes!!

Hunter Mountain 2 Bedroom Condo - Steps to Ski Slopes!!
Hunter Highlands
10.0 out of 10, Exceptional, (19 reviews)
"Excellent stay- we had a great time!"
United States
jyiwest 5.
$367 nightly
The price is $396
Jul 22 - Jul 23
Total with taxes and fees
Hunter Mountain 2 Bedroom Condo - Steps to Ski Slopes!!
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

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?

Experience The Catskill Getaway. Not your typical vacation rental: 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 3 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, 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 Mountain Top Arboretum. 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.