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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is HK$670
HK$1,147 total
includes taxes & fees
25 Aug - 26 Aug
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, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is HK$1,019
HK$1,744 total
includes taxes & fees
26 Aug - 27 Aug
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
The price is HK$941
HK$2,257 total
includes taxes & fees
2 Sept - 3 Sept
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, (311 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
The price is HK$980
HK$1,098 total
includes taxes & fees
25 Aug - 26 Aug
Starlite Motel
A log cabin with a porch, a staircase, and a garage.

5. 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, (29 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is HK$1,019
HK$1,744 total
includes taxes & fees
25 Aug - 26 Aug
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A natural landscape with a lake, rocky cliffs, and a bench.

6. Boutique Glamping Dome in the Catskill Mountains

Boutique Glamping Dome in the Catskill Mountains
Gilboa
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful place to enjoy nature! Peaceful ! Pool time was refreshing! The downside is that the dome gets very hot during the day. At least at night is nice and cold ! But we really enjoyed !"
United States
Heidi
The price is HK$947
HK$1,570 total
includes taxes & fees
25 Aug - 26 Aug
Boutique Glamping Dome in the Catskill Mountains
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

7. 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.
The price is HK$882
HK$1,755 total
includes taxes & fees
27 Aug - 28 Aug
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
A kitchen with green cabinets, a stainless steel stove, and a brick wall.

8. 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.
The price is HK$1,227
HK$2,953 total
includes taxes & fees
26 Aug - 27 Aug
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

9. 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.
The price is HK$1,411
HK$2,904 total
includes taxes & fees
25 Aug - 26 Aug
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A deck with a fire pit, outdoor seating, and a view of the landscape.

10. 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
The price is HK$2,354
HK$4,408 total
includes taxes & fees
1 Sept - 2 Sept
Romantic Catskill Getaway | HotTub w/Mountain View
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

11. 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.
The price is HK$1,215
HK$3,438 total
includes taxes & fees
25 Aug - 26 Aug
West Kill Barnhouse: Ski, Work & Unwind
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

12. 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.
The price is HK$1,725
HK$4,403 total
includes taxes & fees
14 Sept - 15 Sept
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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.

13. 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 HK$1,867
HK$6,318 total
includes taxes & fees
25 Aug - 26 Aug
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

14. 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.
The price is HK$1,717
HK$3,591 total
includes taxes & fees
15 Sept - 16 Sept
MIRROR CABIN IN THE FOREST WITH HOT TUB
A cozy living room with a leather sofa, a fireplace, and a Netflix sign.

15. 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
8.4 out of 10, Very good, (6 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.
The price is HK$978
HK$1,951 total
includes taxes & fees
7 Sept - 8 Sept
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!
A cozy cabin interior with a wooden interior, a spiral staircase, a kitchen area, and a seating area with a view.

16. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.6 out of 10, Exceptional, (29 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is HK$1,568
HK$3,387 total
includes taxes & fees
9 Sept - 10 Sept
Spacious Catskill Mountains ski cabin with fire pit
A living room with a stone fireplace, leather sofa, and a mounted TV displaying 'NETFLIX'.

17. 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, (23 reviews)
"You will definitely return this place is cozy, clean and convenient! "
United States
Elizabeth C.
The price is HK$1,025
HK$2,011 total
includes taxes & fees
31 Aug - 1 Sept
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
A paved pathway with benches and rocks, bordered by neatly trimmed hedges and trees, leading to a building with a visible entrance.

18. Cozy Downtown Hunter Mountain Getaway

Cozy Downtown Hunter Mountain Getaway
Lanesville
6.0 out of 10, (1 review)
"I was disappointed with the condo because the a/c that was listed did not cool the upstairs bedroom. Also, the bed had flannel sheets which made sleeping problematic. I would recommend condo spring, fall and winter.Kitchen table only had a single chair which was a problem,"
United States
Paul J.
The price is HK$699
HK$1,449 total
includes taxes & fees
25 Aug - 26 Aug
Cozy Downtown Hunter Mountain Getaway
A red building with a wooden deck, white chairs, and a view of a lake and hills.

19. 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, (20 reviews)
"Excellent stay- we had a great time!"
United States
jyiwest 5.
The price is HK$1,372
HK$3,150 total
includes taxes & fees
25 Aug - 26 Aug
Hunter Mountain 2 Bedroom Condo - Steps to Ski Slopes!!
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

20. 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.
The price is HK$1,623
HK$4,378 total
includes taxes & fees
22 Sept - 23 Sept
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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

Catskill Seasons Inn

Catskill Seasons Inn

10/10 Excellent
"Easy self check-in, clean room, nice pool, nice fire pit, plenty of parking."
Christian 2-night trip
Posted 3 hours ago
Catskill Seasons Inn

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ashland!

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?

Catskill Mountain Retreat -- private, beautiful views, hot tub, game rm, firepit: This holiday home rental outside of Ashland is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a library and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ashland?

With 4 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 Mountain Resort 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.