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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Ashland vacation rentals

Premium House, Kitchen, Mountain View | Private kitchen | Coffee/tea maker, full-size fridge, microwave

1. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
The price is SAR 469
SAR 526 total
includes taxes & fees
28 Sep - 29 Sep
Starlite Motel
Front of property

2. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
The price is SAR 1,611
SAR 2,036 total
includes taxes & fees
30 Sep - 1 Oct
Windham NY Escape
Property grounds

3. 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 SAR 1,144
SAR 1,987 total
includes taxes & fees
29 Sep - 30 Sep
Romantic Catskill Getaway | HotTub w/Mountain View
Exterior

4. 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
The price is SAR 601
SAR 933 total
includes taxes & fees
28 Sep - 29 Sep
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Sauna

5. 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, (75 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.
The price is SAR 1,521
SAR 2,465 total
includes taxes & fees
28 Sep - 29 Sep
Mountain house with Scandinavian BBQ hut and Hot tub
Interior

6. Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies

Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
Prattsville
9.6 out of 10, Exceptional, (8 reviews)
"The cabin was charming, the kitchen was stocked with tools for cooking, and the wood fired hot tub was magical. It's a perfect place for families or a couple who are looking for a Catskills getaway or are skiing in the area. Would definitely come back."
United States
Bengt A.
The price is SAR 1,397
SAR 2,098 total
includes taxes & fees
1 Oct - 2 Oct
Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
Exterior

7. 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 SAR 287
SAR 513 total
includes taxes & fees
28 Sep - 29 Sep
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Interior

8. 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 SAR 860
SAR 1,562 total
includes taxes & fees
28 Sep - 29 Sep
Midnight Fox
Exterior

9. 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, (34 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
The price is SAR 488
SAR 811 total
includes taxes & fees
28 Sep - 29 Sep
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Smart TV, fireplace, DVD player, books

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.
The price is SAR 1,504
SAR 2,374 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Property grounds

11. 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.
The price is SAR 676
SAR 1,298 total
includes taxes & fees
5 Oct - 6 Oct
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Dining

12. 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 SAR 451
SAR 1,030 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Cabin-Catskills secluded Mountain retreat
Smart TV, fireplace, books

13. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is SAR 1,436
SAR 2,512 total
includes taxes & fees
28 Sep - 29 Sep
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Property grounds

14. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is SAR 1,348
SAR 1,987 total
includes taxes & fees
28 Sep - 29 Sep
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Smart TV, fireplace

15. 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 SAR 1,783
SAR 2,806 total
includes taxes & fees
1 Oct - 2 Oct
Condo in Windham Mountain Village
Exterior

16. 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.
The price is SAR 751
SAR 1,902 total
includes taxes & fees
6 Oct - 7 Oct
Pines Vignette • Modern 3BR Home in Windham
Interior

17. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.6 out of 10, Exceptional, (31 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is SAR 672
SAR 1,428 total
includes taxes & fees
28 Sep - 29 Sep
Spacious Catskill Mountains ski cabin with fire pit
1 bedroom, in-room safe, iron/ironing board, travel crib

18. PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY

PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Windham
The price is SAR 785
SAR 979 total
includes taxes & fees
30 Sep - 1 Oct
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Property grounds

19. Gorgeous Mountains Views & Private Stream in Secluded Oasis

Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gilboa
10.0 out of 10, Exceptional, (8 reviews)
"Our stay was great: attentive host, comfortable lodgings, beautiful setting."
United States
Carrie S.
The price is SAR 676
SAR 1,476 total
includes taxes & fees
27 Oct - 28 Oct
Gorgeous Mountains Views & Private Stream in Secluded Oasis
TV, fireplace

20. 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 SAR 785
SAR 1,922 total
includes taxes & fees
20 Oct - 21 Oct
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

8/10 Good
"Just for starters, our room was very very clean and very nice. Lots of room comfortable, bed. I guess some of the problems were with the outside areas. We noticed outside our patio, a pile of cigarette butts and roaches, and some chipping paint that didn’t appear to have been cleaned up for a while. We arrived on a Tuesday afternoon, though the front desk staff were friendly, just didn’t seem to be overly motivated to accommodate new guests. One of the highlights is the outdoor fire pit, which has a really lovely setting. However, the fire pit was filled with trash that appeared to be pill packages and I’m taking a LOT of them! They weren’t cleaned out, just kind of shoved to the side, we had to ask them the next day if they could clean out the fire pit which they did fairly well. Definitely noticed somewhere and tear on the outside such as chipped and peeling paint on these patios and stairways. Overall, a nice day could just use a little facelift!"
Celia 3-night trip
Posted 12 hours ago
Hunter Lodge, a Bluebird by Lark

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 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.