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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Ashland holiday 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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
The price is AU$174
includes taxes & fees
11 Nov - 12 Nov
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
8.8 out of 10, Excellent, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is AU$276
includes taxes & fees
10 Nov - 11 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Entryway area

3. 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.
The price is AU$696
includes taxes & fees
10 Nov - 11 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A deck with a fire pit, outdoor seating, and a view of the landscape.

4. Romantic Catskill Getaway | HotTub w/Mountain View

Romantic Catskill Getaway | HotTub w/Mountain View
Prattsville
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay! The cabin was clean, cozy, and peaceful, surrounded by beautiful nature. It was the perfect place to relax and enjoy the tranquility. Thank you for your warm hospitality! We would love to come back again."
United States
Alena
The price is AU$642
includes taxes & fees
10 Nov - 11 Nov
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.

5. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AU$677
includes taxes & fees
10 Nov - 11 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

6. Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.8 out of 10, Exceptional, (11 reviews)
"Secluded yet convenient. Homey. Quaint. Loved it! Will stay again!"
United States
Amber C.
The price is AU$394
includes taxes & fees
10 Nov - 11 Nov
Cozy Cabin-Catskills secluded Mountain retreat
A living room with a brick fireplace, leather sofa, and a flat-screen TV.

7. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
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.
The price is AU$286
includes taxes & fees
17 Nov - 18 Nov
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
A cozy living room with wooden walls, a stone fireplace, and a television.

8. 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.
The price is AU$911
includes taxes & fees
17 Nov - 18 Nov
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A spacious dining area with a high ceiling, exposed wooden beams, and hanging light fixtures.

9. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is AU$1,123
includes taxes & fees
15 Nov - 16 Nov
Catskills Escape w/ Hot Tub & Fireplace
A spacious log cabin interior with a high ceiling, wooden floors, a billiards table, and a cozy seating area.

10. 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.
The price is AU$4,562
includes taxes & fees
17 Nov - 18 Nov
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
A cozy outdoor seating area with Adirondack chairs, a fire pit, and a stone fireplace.

11. **Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski

**Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski
Prattsville
9.4 out of 10, Exceptional, (10 reviews)
"The House is beautiful and nicely decorated. the kitchen is fully equipped, great back yard and many games in the game room, the jacuzzi was a great plus and we all gather around the fire pit. We loved the place amazing location and we will be happy to return back again."
United States
Hermine H.
The price is AU$1,971
includes taxes & fees
10 Nov - 11 Nov
**Luxury Catskill MNTN 5BR 3Bath Villa Hot Tub/ Fire Pit,Ski
Front of property

12. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (3 reviews)
"The best "
United States
Miguel
The price is AU$790
includes taxes & fees
10 Nov - 11 Nov
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.

13. 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.
The price is AU$1,093
includes taxes & fees
14 Nov - 15 Nov
Condo in Windham Mountain Village
Living area

14. 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.
The price is AU$870
includes taxes & fees
16 Nov - 17 Nov
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

15. Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (23 reviews)
"Great little cabin with nice atmosphere. It was an awesome place to spend the weekend and enjoy the Catskills. Clean, cozy, and quiet. A nice place to come back to and relax day after day."
United States
Andrea S.
The price is AU$267
includes taxes & fees
19 Nov - 20 Nov
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
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.
The price is AU$2,759
includes taxes & fees
10 Nov - 11 Nov
Lux Mansion, Windham: Hot Tub, Sauna
A house with a fire pit and outdoor seating.

17. 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.
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
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.
The price is AU$609
includes taxes & fees
10 Nov - 11 Nov
Midnight Fox
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

19. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is AU$237
includes taxes & fees
10 Nov - 11 Nov
Starlite Motel
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

20. Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
Windham
7.8 out of 10, Good, (6 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.
The price is AU$452
includes taxes & fees
10 Nov - 11 Nov
Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
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

10/10 Excellent
"We had a great time. The pool, hot tubs and saunas were amazing. The bar and restaurant was very good. No need to drive out of the hotel for a drink or dinner. Just wished the bar was open until later. Bedroom was very nice. We stayed in a deluxe studio and it was nicely stocked with everything we needed. We will definitely be coming back. Planning to come with the family for snow fun."
Alyson 2-night trip
Posted 12 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ashland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as AU$237 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Ashland?

Yes, there are holiday rentals close to the most popular sights in Ashland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ashland has to offer?

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend: This holiday home rental outside of Ashland is located in the mountains, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ashland?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.