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Featured Holiday Homes in Woodstock

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
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 ...
Esopus Creek modern Tiny house Retreat!
The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
Located in Staatsburg, this vacation home is in a rural location, within a 10-minute drive of Margaret Lewis Norrie State Park and Ogden Mills and Ruth Livingston ...
The Farm at Hyde Park
Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia

Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia

2 out of 5
Phoenicia
When you stay at this vacation home in Phoenicia, you'll be in the mountains, within a 15-minute walk of Catskill Mountains and Catskill State Park.
Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia
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Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village

Saugerties
Located in Saugerties, this vacation home is within a 15-minute walk of Esopus Creek and Kiersted House.
Brand New House w gated backyard that is located right at the Saugerties Village
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

Prattsville
Located in Prattsville, this vacation home is on the waterfront, a 1-minute drive from Catskill State Park and 9 minutes from Prattsville Town Hall.
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
HOT TUB w/ POOL,  STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Woodstock
A stay at this vacation home places you in the heart of Woodstock, steps from Catskill State Park and a 4-minute drive from Woodstock Public Library.
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Woodstock Ski House on 35 private acres Mtn Views

Woodstock Ski House on 35 private acres Mtn Views

Woodstock
Located in Bearsville, this vacation home is in the mountains, a 1-minute drive from Catskill State Park and 7 minutes from Byrdcliffe Barn.
Woodstock Ski House on 35 private acres Mtn Views
Higashi: New Paltz family home with King bed minutes to downtown

Higashi: New Paltz family home with King bed minutes to downtown

New Paltz
Located in New Paltz, this vacation home is within a 5-minute drive of Historic Huguenot Street and Huguenot Street Historic District.
Higashi: New Paltz family home with King bed minutes to downtown
Charming Catskill getaway walking distance to Main St. Pet-friendly!

Charming Catskill getaway walking distance to Main St. Pet-friendly!

Catskill
With a stay at this vacation home in Catskill, you'll be a 5-minute walk from Thomas Cole National Historic Site and 7 minutes by foot from Greene County Council ...
Charming Catskill getaway walking distance to Main St. Pet-friendly!
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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.

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

Holiday houses in Woodstock 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 Woodstock 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 Woodstock adventures, obvs.

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

Woodstock Holiday Homes essential information

Accommodation
1009 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Esopus Creek modern Tiny house Retreat!, The Farm at Hyde Park, Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia, Brand New House w gated backyard that is located right at the Saugerties Village, Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking., HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN, Woodstock Ski House on 35 private acres Mtn Views, Higashi: New Paltz family home with King bed minutes to downtown, Charming Catskill getaway walking distance to Main St. Pet-friendly!

Top trending hotels in Woodstock

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
When you a stay at Woodstock Way Hotel in Woodstock, you'll be on the waterfront, just steps from Catskill State Park and Woodstock Artists Association and ...
Woodstock Way Hotel
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St, Woodstock, NY
Twin Gables of Woodstock is in the heart of Woodstock, within a 5-minute walk of Woodstock Public Library and Woodstock Music Shop.
Twin Gables of Woodstock
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
When you a stay at The Herwood Inn in Woodstock, you'll be in the mountains, just steps from Catskill State Park and The Comeau Property.
The Herwood Inn
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Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
With a stay at Hotel Dylan in Woodstock, you'll be next to a golf course, just steps from Catskill State Park and a 4-minute drive from Ashokan Rail Trail- Woodstock ...
Hotel Dylan
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^Subject to availability and chosen travel dates.