Book Holiday Homes in Shandaken

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Featured Holiday Homes in Shandaken

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston NY
The price is AU$388 per night from 20 Jan to 21 Jan
AU$388
20 Jan - 21 Jan 2026
includes taxes & fees
With a stay at this vacation home in Kingston, you'll be on a river, just steps from Catskill State Park and a 4-minute drive from Thorn Preserve - Catskill ...
Opens in a new windowEsopus Creek modern Tiny house Retreat!
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 NY
The price is AU$815 per night from 30 Dec to 31 Dec
AU$815
30 Dec - 31 Dec
includes taxes & fees
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.
Opens in a new windowA world where time stands still, close to Belleayre Ski & Wedding venues.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville NY
With a stay at this vacation home in Bearsville, you'll be in the mountains, within a 15-minute drive of Catskill Mountains and Catskill State Park.
Opens in a new windowLuxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
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Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing

Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing

Jewett NY
With a stay at this vacation home in Hunter, you'll be within a 15-minute drive of Hunter Mountain and Windham Mountain Resort.
Opens in a new windowMaplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Lanesville NY
With a stay at this vacation home in Hunter, you'll be on the waterfront, within a 5-minute drive of Hunter Mountain and Catskill State Park.
Opens in a new windowBest rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location
Secluded  family retreat within minutes of Woodstock village

Secluded family retreat within minutes of Woodstock village

Woodstock NY
Located in Saugerties, this vacation home is in the mountains, a 1-minute drive from Catskill State Park and 5 minutes from Opus 40.
Opens in a new windowSecluded family retreat within minutes of Woodstock village
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

Windham NY
With a stay at this vacation home in Windham, you'll be in the mountains, within a 10-minute drive of Windham Mountain Resort and Windham Country Club.
Opens in a new windowTimber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
Birch Creek Mountain House- 3 minutes to Belleayre Mtn

Birch Creek Mountain House- 3 minutes to Belleayre Mtn

Big Indian NY
When you stay at this vacation home in Pine Hill, you'll be on the waterfront, within a 5-minute drive of Catskill Mountains and Belleayre Mountain Ski ...
Opens in a new windowBirch Creek Mountain House- 3 minutes to Belleayre Mtn
StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

Catskill NY
Located in Palenville, this vacation home is a 1-minute drive from Catskill State Park and 5 minutes from Vinnie's Farm Market.
Opens in a new windowStarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes
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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.

Shandaken 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 Shandaken vacation homes are the perfect way for you to wing it.

Holiday houses in Shandaken 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 Shandaken 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 Shandaken adventures, obvs.

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

Shandaken Holiday Homes essential information

Accommodation
729 Holiday Homes
Lowest Price
AU$249
Highest Price
AU$815
Popular accommodation
Esopus Creek modern Tiny house Retreat!, A world where time stands still, close to Belleayre Ski & Wedding venues. , Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat, Maplewood Manor, 8BR w/ Hot Tub, Gym, Fire Pit, Near Hunter/Windham Skiing, Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location, Secluded family retreat within minutes of Woodstock village, Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!, Birch Creek Mountain House- 3 minutes to Belleayre Mtn, StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

Top trending hotels in Shandaken

Catskill Seasons Inn

Catskill Seasons Inn

2.5 out of 5
178 Route 42 Shandaken NY
The price is AU$249 per night from 11 Jan to 12 Jan
AU$249
11 Jan - 12 Jan 2026
includes taxes & fees
With a stay at Catskill Seasons Inn in Shandaken, you'll be within a 15-minute drive of Catskill Mountains and Belleayre Mountain Ski Center.
Opens in a new windowCatskill Seasons Inn
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 AU$275 per night from 5 Jan to 6 Jan
AU$275
5 Jan - 6 Jan 2026
includes taxes & fees
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.
Opens in a new windowHunter 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.
Opens in a new windowHotel Vienna
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AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
The price is AU$328 per night from 4 Jan to 5 Jan
AU$328
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Saugerties, AutoCamp Catskills is in the mountains, within a 10-minute drive of Opus 40 and Bethel Woods Museum.
Opens in a new windowAutoCamp Catskills
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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.