Book Holiday Homes in Ashland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Ashland

Quaint Cottage with Peloton Bike & Sauna near Skiing

Quaint Cottage with Peloton Bike & Sauna near Skiing

Mount Tremper
The price is AU$625 per night from 16 Feb to 17 Feb
AU$625
includes taxes & fees
16 Feb - 17 Feb
With a stay at this vacation home in Mount Tremper, you'll be in the mountains, within a 10-minute drive of Catskill Mountains and Catskill State Park.
Quaint Cottage with Peloton Bike & Sauna near Skiing
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

2 out of 5
Windham
With a stay at this vacation home in Windham, you'll be within a 10-minute drive of Windham Mountain Resort and Catskill State Park.
Magical Home Located in Windham and Catskills
The Tipsy Gypsy

The Tipsy Gypsy

Hunter
The price is AU$722 per night from 29 Jan to 30 Jan
AU$722
includes taxes & fees
29 Jan - 30 Jan
With a stay at this vacation home in Hunter, you'll be within a 5-minute drive of Hunter Mountain and Catskill State Park.
The Tipsy Gypsy
Save an average of 15% on thousands of hotels when you're signed in
 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
The price is AU$233 per night from 29 Jan to 30 Jan
AU$233
includes taxes & fees
29 Jan - 30 Jan
With a stay at this vacation home, you'll be centrally located in Windham, within a 5-minute drive of Windham Mountain Resort and Catskill State Park.
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres,  Ski Lodge

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Windham
With a stay at this vacation home in Windham, you'll be on a river, within a 10-minute drive of Windham Mountain Resort and Catskill State Park.
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

Hunter
The price is AU$808 per night from 18 Feb to 19 Feb
AU$808
includes taxes & fees
18 Feb - 19 Feb
With a stay at this vacation home in Hunter, you'll be in the mountains, within a 5-minute drive of Hunter Mountain and Catskill State Park.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail

Hobart
The price is AU$510 per night from 6 Feb to 7 Feb
AU$510
includes taxes & fees
6 Feb - 7 Feb
When you stay at this vacation home in Hobart, you'll be in the mountains, within a 5-minute drive of Stamford Town Hall and Hobart Book Village.
Cozy Country Farmhouse Along the Catskill Scenic Trail
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Fleischmanns
The price is AU$492 per night from 2 Feb to 3 Feb
AU$492
includes taxes & fees
2 Feb - 3 Feb
Located in Fleischmanns, this vacation home is within a 15-minute drive of Belleayre Mountain Ski Center and Catskill Mountains.
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit
A world where time stands still, close to Belleayre Ski & Wedding venues.

A world where time stands still, close to Belleayre Ski & Wedding venues.

City Roxbury
Located in Denver, this vacation home is in the mountains, a 5-minute drive from East Branch Delaware River and 8 minutes from Pakatakan Farmers' Market.
A world where time stands still, close to Belleayre Ski & Wedding venues.
Don't see what you're looking for?
See all available properties in Ashland
View all properties
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.

Ashland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Ashland vacation homes are the perfect way for you to wing it.

Holiday houses in Ashland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Ashland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Ashland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Ashland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Ashland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Ashland Holiday Homes essential information

Accommodation
497 Holiday Homes
Lowest Price
AU$233
Highest Price
AU$808
Popular accommodation
Quaint Cottage with Peloton Bike & Sauna near Skiing, Magical Home Located in Windham and Catskills, The Tipsy Gypsy, Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter, Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge, SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!, Cozy Country Farmhouse Along the Catskill Scenic Trail, Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit, A world where time stands still, close to Belleayre Ski & Wedding venues.

Top trending hotels in Ashland

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
The price is AU$315 per night from 29 Jan to 30 Jan
AU$315
includes taxes & fees
29 Jan - 30 Jan
With a stay at Hunter Lodge, a Bluebird by Lark in Hunter, you'll be near ski lifts, within a 5-minute drive of Hunter Mountain and Catskill State Park.
Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
When you stay at Hotel Vienna in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Country Club and Windham Mountain Resort.
Hotel Vienna
The Roxbury

The Roxbury

3 out of 5
2258 Co Rd 41, Roxbury, NY
With a stay at The Roxbury in Roxbury, you'll be next to a golf course, just a 1-minute walk from East Branch Delaware River and 6 minutes by foot from Roxbury ...
The Roxbury
Save an average of 15% on thousands of hotels when you're signed in
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
37 Alpine Rd, Big Indian, NY
The price is AU$407 per night from 29 Jan to 30 Jan
AU$407
includes taxes & fees
29 Jan - 30 Jan
With a stay at Urban Cowboy Lodge in Big Indian, you'll be on a river, within a 10-minute drive of Catskill Mountains and Catskill State Park.
Urban Cowboy Lodge
Don't see what you're looking for?
See all available properties in Ashland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.