Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

 Beautiful new house 3/4  mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain

hunter
Book a stay at this family-friendly vacation home in Hunter. Enjoy a garden, a pool table, and patios. Popular attractions Hunter Mountain and Windham Mountain ...
Beautiful new house 3/4 mile from Hunter Mountain
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
The price is NZ$804 per night from 21 Apr to 22 Apr
NZ$804
includes taxes & fees
21 Apr - 22 Apr
Stay at this vacation home in Denver. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Pakatakan Farmers' Market and Plattekill State Forest ...
A world where time stands still, close to Belleayre Ski & Wedding venues.
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

Fleischmanns
Stay at this vacation home in Fleischmanns. Enjoy free WiFi, a garden, and patios. Popular attractions Belleayre Mountain Ski Center and Pakatakan Farmers' Market ...
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
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SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

Hunter
Stay at this vacation home in Hunter. Enjoy free WiFi, a garden, and patios. Popular attractions Hunter Mountain and H Ski Lift are located nearby.
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

Windham
Book a stay at this ski vacation home in Windham. Enjoy free WiFi, a water park, and a garden. Popular attractions Windham Mountain Resort and Ashland Park are ...
A'Neils Windham Ski Lodge & Family Retreat
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

Lanesville, Hunter
The price is NZ$1,535 per night from 5 May to 6 May
NZ$1,535
includes taxes & fees
5 May - 6 May
Book a stay at this beach vacation home in Hunter. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hunter Mountain and Windham Mountain ...
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim
Catskills Cozy Cottage with Peloton & Sauna near Hunter  and Belleayre Mountain

Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain

Mount Tremper
The price is NZ$451 per night from 21 Apr to 22 Apr
NZ$451
includes taxes & fees
21 Apr - 22 Apr
Stay at this vacation home in Mount Tremper. Enjoy a fitness center, a garden, and an in-room coffeemaker. Popular attractions Mount Tremper Arts and Emerson ...
Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain
◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna

◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna

Hunter
Stay at this vacation home in Lexington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Windham Mountain Resort and Ashland Park are located ...
◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna
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
The price is NZ$333 per night from 27 Apr to 28 Apr
NZ$333
includes taxes & fees
27 Apr - 28 Apr
Stay at this vacation home in Windham. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Windham Mountain Resort and Windham Country ...
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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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
629 Holiday Homes
Lowest Price
NZ$228
Highest Price
NZ$1,535
Popular accommodation
Beautiful new house 3/4 mile from Hunter Mountain , A world where time stands still, close to Belleayre Ski & Wedding venues. , Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub, SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!, A'Neils Windham Ski Lodge & Family Retreat, 7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim, Catskills Cozy Cottage with Peloton & Sauna near Hunter and Belleayre Mountain, ◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna, TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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
Fully refundableReserve now, pay when you stay
The price is NZ$289 per night from 21 Apr to 22 Apr
NZ$289
includes taxes & fees
21 Apr - 22 Apr
Stay at this 3-star hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hunter Lodge, a Bluebird by Lark
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
37 Alpine Rd, Big Indian, NY
The price is NZ$521 per night from 21 Apr to 22 Apr
NZ$521
includes taxes & fees
21 Apr - 22 Apr
Stay at this 5-star luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions ...
Urban Cowboy Lodge
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hotel Vienna
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The Roxbury at Stratton Falls

The Roxbury at Stratton Falls

2 out of 5
48 Co Rd 41, Roxbury, NY
The price is NZ$228 per night from 4 May to 5 May
NZ$228
includes taxes & fees
4 May - 5 May
Stay at this hotel in Roxbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Plattekill State Forest and Plattekill Mountain are located ...
The Roxbury at Stratton Falls
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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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^Subject to availability and chosen travel dates.