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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Ashland vacation rentals

Interior

1. Cozy 1-bedroom studio in peaceful Ashland with AC

Cozy 1-bedroom studio in peaceful Ashland with AC
Ashland
$322 nightly
The price is $348
Oct 4 - Oct 5
Total with taxes and fees
Cozy 1-bedroom studio in peaceful Ashland with AC
A wooden interior with a central fireplace, benches, and a window offering a forest view.

2. 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 two-story building with large windows and a storefront.

3. 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
An outdoor patio area with a pergola, seating, and a barbecue grill.

4. The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Ashland
$532 nightly
The price is $575
Oct 14 - Oct 15
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
A two-story building with large windows and a storefront.

5. 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
$238 nightly
The price is $257
Oct 5 - Oct 6
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A deck with a fire pit, outdoor seating, and a view of the landscape.

6. 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
Oct 4 - Oct 5
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
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.
$491 nightly
The price is $530
Oct 27 - Oct 28
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 5 - Oct 6
Total with taxes and fees
Windham NY Escape
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

9. 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.
$947 nightly
The price is $1,023
Oct 4 - Oct 5
Total with taxes and fees
Condo in Windham Mountain Village
A cozy living room with wooden walls, a stone fireplace, and a television.

10. 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.
$624 nightly
The price is $673
Oct 6 - Oct 7
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A spacious log cabin interior with a high ceiling, wooden floors, a billiards table, and a cozy seating area.

11. Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
$3,141 nightly
The price is $3,392
Oct 10 - Oct 11
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

12. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (315 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Oct 5 - Oct 6
Total with taxes and fees
Starlite Motel
Dining

13. 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 wooden dining area with a fireplace, large windows, and a chandelier.

14. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
10.0 out of 10, Exceptional, (9 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
$1,527 nightly
The price is $1,649
Oct 4 - Oct 5
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

15. 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 4 - Oct 5
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
A bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a sink and mirror.

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

Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
Windham
$248 nightly
The price is $283
Oct 5 - Oct 6
Total with taxes and fees
Presidential Duplex with Jacuzzi, Steam Shower and Private Terrace
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

17. 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, (11 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.
$340 nightly
The price is $367
Oct 5 - Oct 6
Total with taxes and fees
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

18. 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 27 - Oct 28
Total with taxes and fees
Midnight Fox
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.

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.
$677 nightly
The price is $731
Oct 4 - Oct 5
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

20. 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.
$377 nightly
The price is $407
Oct 5 - Oct 6
Total with taxes and fees
West Kill Barnhouse: Ski, Work & Unwind
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

Starlite Motel

Starlite Motel

10/10 Excellent
"Cute motel! Had updated bathroom. Also, had a kitchen with full refrigerator. Unfortunately, because of the rain we did not get to experience the grill, picnic area and fire pit out back. Location is great if you want to do some heavy duty hiking....lots of hikes/trailheads within 30 minutes of Starlite. Michelle reached out prior to our arrival with very helpful information. My only complaint was that the beds were a little too soft for me....had foam topper. I highly recommend the Phoenicia Diner (15 min away), Woodstock Brewery (15 min away...has good food, too) and Peekamoose (2 min away)."
Lisa 2-night trip
Posted 3 days ago
Starlite Motel

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 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.