Ashland Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Ashland holiday rentals

Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (29 reviews)
"Best place ever!!"
United States
LaurapatOsterwald S.
The price is HK$1,583
HK$2,883 total
includes taxes & fees
18 Feb - 19 Feb
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Dining

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (17 reviews)
"Best gateway "
United States
Michael D.
The price is HK$1,352
HK$3,723 total
includes taxes & fees
18 Feb - 19 Feb
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Exterior

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Mt. Tremper
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful spot to unwind and take a relaxing getaway."
United States
cheryll s.
The price is HK$1,329
HK$3,064 total
includes taxes & fees
23 Feb - 24 Feb
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Property grounds

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

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Phoenicia
The price is HK$1,125
HK$2,223 total
includes taxes & fees
18 Feb - 19 Feb
"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Bar (on property)

Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is HK$922
HK$1,589 total
includes taxes & fees
19 Feb - 20 Feb
Jessie's Harvest House
Interior

Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.8 out of 10, Exceptional, (20 reviews)
"The house was exactly what we were looking for! Close to the ski mountains, town and made for a really nice weekend away!"
United States
Lauren P.
The price is HK$1,400
HK$3,132 total
includes taxes & fees
18 Feb - 19 Feb
Spacious Catskill Mountains ski cabin with fire pit
Dining

Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.6 out of 10, Exceptional, (5 reviews)
"Great place to get away. "
United States
Joshua
The price is HK$922
HK$2,223 total
includes taxes & fees
23 Feb - 24 Feb
Cozy Cabin-Catskills secluded Mountain retreat
Sauna

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (35 reviews)
"The furnishings were cute and quaint. The beds were very comfy."
United States
Jan
The price is HK$1,250
HK$2,766 total
includes taxes & fees
19 Feb - 20 Feb
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
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, (69 reviews)
"Very clean and well located"
United States
Dana S.
The price is HK$978
HK$2,262 total
includes taxes & fees
25 Feb - 26 Feb
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, (11 reviews)
"Michael is a great host. Check-in was super easy and the cabin is pretty clean:) "
United States
Bainan X.
The price is HK$1,055
HK$1,952 total
includes taxes & fees
1 Mar - 2 Mar
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Microwave, oven, stovetop, dishwasher

Little red house just outside of Woodstock

Little red house just outside of Woodstock
Bearsville
9.0 out of 10, Wonderful, (2 reviews)
"The house is cute, well decorated but very small "
United States
Harry
The price is HK$2,286
HK$4,372 total
includes taxes & fees
21 Feb - 22 Feb
Little red house just outside of Woodstock
Exterior

Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake

Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
East Jewett
10.0 out of 10, Exceptional, (13 reviews)
"What a beautiful vibe for a romantic getaway! Property was so clean and has everything we had to relax! The owners are super courteous. Would definitely come back!"
United States
Patrick F.
The price is HK$2,345
HK$4,583 total
includes taxes & fees
1 Mar - 2 Mar
Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
Private kitchen

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (287 reviews)
"A perfect place to stay by the Mt"
United States
Oleg
The price is HK$977
HK$1,094 total
includes taxes & fees
23 Feb - 24 Feb
Starlite Motel
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (124 reviews)
"Excellent stay! Very clean with everything we needed. Loved the sauna! Thank you for an excellent weekend stay."
United States
Christine S.
The price is HK$1,400
HK$2,477 total
includes taxes & fees
18 Feb - 19 Feb
Sauna Belleayre Cozy Cabin
Exterior

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.0 out of 10, Wonderful, (20 reviews)
"Beautiful location in a well kept property! Highly recommend it."
United States
Robert
The price is HK$1,485
HK$2,321 total
includes taxes & fees
18 Feb - 19 Feb
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Outdoor dining

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (1 review)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
The price is HK$886
HK$1,605 total
includes taxes & fees
2 Mar - 3 Mar
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
2 bedrooms, travel cot, free WiFi, bed sheets

Renovated Barnhouse Escape

Renovated Barnhouse Escape
Lanesville
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, easy check in and communication, quiet, and clean. Only stayed one night but had a great time. The hike to the falls from the trailhead at the end of the road is a nice plus. "
United States
Robert T.
The price is HK$1,165
HK$2,558 total
includes taxes & fees
8 Mar - 9 Mar
Renovated Barnhouse Escape
Interior

Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre

Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre
Jefferson
10.0 out of 10, Exceptional, (4 reviews)
"It was just as described and just what we needed!"
United States
Lawrence J.
The price is HK$1,555
HK$3,579 total
includes taxes & fees
18 Feb - 19 Feb
Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre
Property grounds

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$1,211
HK$2,566 total
includes taxes & fees
9 Mar - 10 Mar
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Smart TV, fireplace

Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors
Hensonville
10.0 out of 10, Exceptional, (2 reviews)
"Good experience the agent saqib was excellent and very helpful "
United States
Rabih
The price is HK$849
HK$4,986 total
includes taxes & fees
3 Mar - 4 Mar
Relaxing Mountain Hideaway - Hot Tub & Outdoors
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 Colonial Motel

The Colonial Motel

10/10 Excellent
"All good"
Oleksandr 1-night trip
Posted 2 days ago
The Colonial Motel

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:

  • View our selection of featured holiday rentals in Ashland
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  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

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?

⭐ Spacious Lake House Just Minutes From The Slopes ⭐: This holiday home rental outside of Ashland is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Ashland?

With 5 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 Irish Cultural Center. Ashland Town Hall and Hunter Mountain 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.