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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Ashland holiday 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 NZ$509
includes taxes & fees
29 June - 30 June
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 NZ$430
includes taxes & fees
5 July - 6 July
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 NZ$458
includes taxes & fees
9 July - 10 July
Sauna Belleayre Cozy Cabin
Sauna

Vintage camper on small farm

Vintage camper on small farm
Greenville
The price is NZ$296
includes taxes & fees
29 June - 30 June
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 NZ$498
includes taxes & fees
5 July - 6 July
Cozy Cabin-Catskills secluded Mountain retreat
Suite, 2 Bedrooms | Living area

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 NZ$280
includes taxes & fees
29 June - 30 June
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, (23 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is NZ$712
includes taxes & fees
29 June - 30 June
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 NZ$508
includes taxes & fees
29 June - 30 June
"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 NZ$339
includes taxes & fees
29 June - 30 June
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 NZ$242
includes taxes & fees
29 June - 30 June
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Premium House, Kitchen, Mountain View | Private kitchen

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 NZ$248
includes taxes & fees
1 July - 2 July
Starlite Motel
Terrace/patio

Mountainside Catskills Cabin | Hike - Fish - Relax

Mountainside Catskills Cabin | Hike - Fish - Relax
Phoenicia
The price is NZ$952
includes taxes & fees
29 June - 30 June
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 NZ$648
includes taxes & fees
6 July - 7 July
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 NZ$508
includes taxes & fees
29 June - 30 June
"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 NZ$437
includes taxes & fees
6 July - 7 July
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, (23 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is NZ$377
includes taxes & fees
29 June - 30 June
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, (1 review)
"cute little spot! very nice place to stay"
United States
David R.
The price is NZ$370
includes taxes & fees
30 June - 1 July
Jessie's Harvest House
Fridge, microwave, oven, stovetop

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 NZ$387
includes taxes & fees
6 July - 7 July
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
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 NZ$990
includes taxes & fees
29 June - 30 June
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

The Hidden Inn

The Hidden Inn

10/10 Excellent
"Room was very clean and owners were very helpful."
Stephen 1-night trip
Posted 12 hours ago
The Hidden Inn

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?

The Hog Mountain Chalet • Hot Tub • Near Belleayre: This holiday home rental outside of Ashland is located in the mountains, and has a fireplace, a balcony 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 selection of games 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.