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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Ashland vacation rentals

Smart TV, fireplace, books, stereo

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Fleischmanns
9.6 out of 10, Exceptional, (76 reviews)
"Everything was good for our stay"
United States
jesse u.
The price is AED 459
AED 1,063 total
includes taxes & fees
30 Jun - 1 Jul
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Fridge, microwave, oven, stovetop

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.
The price is AED 479
AED 903 total
includes taxes & fees
5 Jul - 6 Jul
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (131 reviews)
"Very cozy and comfortable, super close toBelleayre. We enjoyed the sauna after a day of skiing. Thank you for an amazing stay! "
United States
Taku T.
The price is AED 502
AED 981 total
includes taxes & fees
13 Jul - 14 Jul
Sauna Belleayre Cozy Cabin
Sauna

Vintage camper on small farm

Vintage camper on small farm
Greenville
The price is AED 347
AED 613 total
includes taxes & fees
30 Jun - 1 Jul
Vintage camper on small farm
Dining

Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.6 out of 10, Exceptional, (9 reviews)
"Great place to get away. "
United States
Joshua
The price is AED 433
AED 1,037 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Cabin-Catskills secluded Mountain retreat
Suite, 2 Bedrooms | Living area | TV

Suites on Main

Suites on Main
3.0 star property
Margaretville
7.2 out of 10, Good, (80 reviews)
"Great room, good amenities, very nice area. My friends and I had a great time staying here for our skiing trip and plan on renting again next year."
United States
Taylor
The price is AED 400
AED 580 total
includes taxes & fees
30 Jun - 1 Jul
Suites on Main
Interior

Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.6 out of 10, Exceptional, (24 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is AED 658
AED 1,472 total
includes taxes & fees
30 Jun - 1 Jul
Spacious Catskill Mountains ski cabin with fire pit
Property grounds

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Phoenicia
The price is AED 560
AED 1,085 total
includes taxes & fees
6 Jul - 7 Jul
"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Property grounds

Boutique Glamping Dome in the Catskill Mountains

Boutique Glamping Dome in the Catskill Mountains
Gilboa
10.0 out of 10, Exceptional, (1 review)
The price is AED 540
AED 847 total
includes taxes & fees
7 Jul - 8 Jul
Boutique Glamping Dome in the Catskill Mountains
Exterior

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 AED 281
AED 502 total
includes taxes & fees
30 Jun - 1 Jul
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Premium House, Kitchen, Mountain View | Private kitchen | Full-size fridge, microwave, coffee/tea maker

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (305 reviews)
"Perfect for us- so close to the mountain and kitchen was great "
United States
Elizabeth
The price is AED 459
AED 514 total
includes taxes & fees
1 Jul - 2 Jul
Starlite Motel
Terrace/patio

Mountainside Catskills Cabin | Hike - Fish - Relax

Mountainside Catskills Cabin | Hike - Fish - Relax
Phoenicia
The price is AED 1,172
AED 1,971 total
includes taxes & fees
30 Jun - 1 Jul
Mountainside Catskills Cabin | Hike - Fish - Relax
Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (32 reviews)
"Lovely place almost magical ....the perfect get away . . So well kept."
United States
Nivia
The price is AED 744
AED 1,367 total
includes taxes & fees
6 Jul - 7 Jul
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Property grounds

"A Stone's Throw" Cabin • Creekside • Fires • BBQ • Fishing

"A Stone's Throw" Cabin • Creekside • Fires • BBQ • Fishing
Phoenicia
8.0 out of 10, Very Good, (3 reviews)
"The host was good and responsive and very accommodating. The location and cabin was beautiful, I highly recommend and will return. "
United States
Alan-Michael N.
The price is AED 529
AED 1,045 total
includes taxes & fees
30 Jun - 1 Jul
"A Stone's Throw" Cabin • Creekside • Fires • BBQ • Fishing
Outdoor dining

Off-Grid Tiny Cabin with Cozy Vintage Charm

Off-Grid Tiny Cabin with Cozy Vintage Charm
Bovina
10.0 out of 10, Exceptional, (5 reviews)
"This was an awesome experience . Loved it Sooo Cozy , Peaceful and Beautiful Cabin . Had a wonderful time and great host Kim Definitely will come back.."
United States
LILLIAN R.
The price is AED 275
AED 921 total
includes taxes & fees
6 Jul - 7 Jul
Off-Grid Tiny Cabin with Cozy Vintage Charm
Exterior

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, (25 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is AED 459
AED 789 total
includes taxes & fees
30 Jun - 1 Jul
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Bar (on property)

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.
The price is AED 492
AED 802 total
includes taxes & fees
30 Jun - 1 Jul
Jessie's Harvest House
2 bedrooms, bed sheets

Cold Spring Lodge - Cabin 2

Cold Spring Lodge - Cabin 2
Big Indian
9.6 out of 10, Exceptional, (4 reviews)
"We had a nice relaxing stay"
United States
Michael
The price is AED 404
AED 823 total
includes taxes & fees
6 Jul - 7 Jul
Cold Spring Lodge - Cabin 2
Outdoor dining

Idyllic Geodesic Dome Sanctuary near Schoharie Creek in New York

Idyllic Geodesic Dome Sanctuary near Schoharie Creek in New York
Gilboa
The price is AED 589
AED 751 total
includes taxes & fees
30 Jun - 1 Jul
Idyllic Geodesic Dome Sanctuary near Schoharie Creek in New York
Property grounds

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, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is AED 1,319
AED 2,051 total
includes taxes & fees
30 Jun - 1 Jul
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
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

Shandaken Inn

Shandaken Inn

10/10 Excellent
"Amazing property and we'll definitely be back. Wasn't quite sure what to expect but it exceeded our expectations in every way. Gorgeous property. Super-comfy bed & duvet. Great pool. Staff & food were fantastic too, especially the trout omlette for breakfast. About a 25-minutes west of Woodstock. Also has a Chargepoint EV charger on property for overnight vehicle charging at super-low rates."
John 1-night trip
Posted 21 hours ago
Shandaken Inn

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?

The Hog Mountain Chalet • Hot Tub • Near Belleayre: This vacation home near Ashland is located in the mountains and has a fireplace, a balcony, 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.