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Search Vacation Homes in Woodstock

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Featured Vacation Homes in Woodstock

Stay and Play! Walk to Town, Onsite Restaurant, Golf Included
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Located in the heart of Woodstock, this historic vacation home is within a 15-minute walk of Woodstock Golf Club and Woodstock Public Library. Thorn Preserve ...

4.3/5Excellent! (3 reviews)
Great!!!

"Had some girls that work for me stay there while we showed at hits in Saugerties ny. Jen was great at responding when I reached out. Will definitely use it again!!!"…"

Reviewed on Sep 5, 2020

Stay and Play! Walk to Town, Onsite Restaurant, Golf Included
Event-friendly Home - 5 Mins to Central Woodstock
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Situated in the mountains, this vacation home is 1.9 mi (3 km) from Woodstock Public Library and 1.9 mi (3.1 km) from Woodstock Golf Club. Overlook Mountain ...

4.9/5Exceptional! (21 reviews)
Much Needed Quiet Time

"Good kitchen, good fireplace, good house, good trees. Just... good."…"

Reviewed on Mar 18, 2020

Event-friendly Home - 5 Mins to Central Woodstock
Peaceful Woodstock Retreat - Restored Barn
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Situated in Woodstock, this vacation home is within 3 mi (5 km) of Woodstock Golf Club, Thorn Preserve - Catskill Center, and Woodstock Public Library. Ashokan ...

5/5Exceptional! (3 reviews)
The great escape

"My husband and I spent a few terrific days in this cute, quirky and cozy house. Our goal was a simple one: escape from NYC and to spend time in nature and try to experience a little normalcy in unique times. We enjoyed spending time in the living room, which was an awesome space that allowed great ..."…"

Reviewed on May 20, 2020

Peaceful Woodstock Retreat - Restored Barn

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Cottonwood-a Luxury Woodstock Home Located Between Woodstock + Saugerties
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Situated in Woodstock, this vacation home is within 3 mi (5 km) of Woodstock Golf Club, Opus 40, and Thorn Preserve - Catskill Center. Woodstock Public Library ...

5/5Exceptional! (6 reviews)
Fantastic fall getaway

"Like many families, we were looking for a long weekend away for a change of scenery. And what a change it was. The house is amazing. Clean and impeccably decorated. The location is superb, very close to restaurants and attractions but far enough removed. The grounds are fantastic, large well manicured ..."…"

Reviewed on Sep 28, 2020

Cottonwood-a Luxury Woodstock Home Located Between Woodstock + Saugerties
Back ON THE Market - Spend This Time in the Heart of Woodstock
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Situated in Woodstock, this historic vacation home is 0.8 mi (1.4 km) from Woodstock Golf Club and 1.6 mi (2.7 km) from Woodstock Public Library. Thorn Preserve ...

5/5Exceptional! (74 reviews)
Secluded Woodstock Home But Minutes from Town

"This property is secluded but still very close to town. The beauty of the lot is spectacular - you truly feel like you are deep in the woods while Main Street is a 5 minute drive away. The house is spacious and has all the comforts and amenities to make our family of 5 feel immediately at home - ..."…"

Reviewed on Sep 14, 2020

Back ON THE Market - Spend This Time in the Heart of Woodstock
'casa Reál' ~ Expansive Woodstock House W/hot Tub!
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Situated in a rural location, this vacation home is within 3 mi (5 km) of Woodstock Golf Club, Thorn Preserve - Catskill Center, and Woodstock Public Library. ...

4.9/5Exceptional! (21 reviews)
A lovely retreat

"We had a wonderful stay at Casa Reál. The house is great and the grounds pretty private, which is what we were looking for coming from the city. The kitchen was fully stocked with everything we needed for a lot of cooking, beds were super comfortable, and everything very clean. We loved the hot tub ..."…"

Reviewed on Sep 12, 2020

'casa Reál' ~ Expansive Woodstock House W/hot Tub!
Heart of Woodstock Unique Arts-and-crafts Home: Outdoor Room and Heated Pool!
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Situated in the mountains, this vacation home is within 3 mi (5 km) of Woodstock Public Library, Woodstock Golf Club, and Overlook Mountain Trailhead. Karma ...

5/5Exceptional! (18 reviews)
5 Star Stay!

"Greg's property goes above and beyond - his place is immaculate (super important!)! The layout of the home was great - plenty of room in the kitchen, easy access to the grill and amazing pool, and the showstopper - the outdoor living room with fireplace and sofas! Get ready to spend your evenings ..."…"

Reviewed on Sep 18, 2020

Heart of Woodstock Unique Arts-and-crafts Home: Outdoor Room and Heated Pool!
Woodstock Historic Artist Estate, The Pond House
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This family-friendly Woodstock vacation home is located on the waterfront, within 1 mi (2 km) of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain ...

5/5Exceptional! (2 reviews)
Incredible house

"We had the most incredible time at this beautiful property- the house and interior are impeccably designed and the land is idyllic (beautiful stream, and gorgeous hiking trail right next to it.) We had a blast grilling our food outdoors, enjoying the fireplace, and going into town which is only 5 ..."…"

Reviewed on May 28, 2020

Woodstock Historic Artist Estate, The Pond House
Woodstock Historic Artist Estate - The Cottage House
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This family-friendly Woodstock vacation home is located on a river, within 1 mi (2 km) of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain ...

4.9/5Exceptional! (16 reviews)
Tranquil and beautiful private getaway with full stream access on Brook and only minutes from town!

"The owners of this property were kind and welcoming. The house was well appointed with most kitchen and bathroom goods one might need. The place was immaculately cleaned as promised due to the COVID-19 health concerns. The decor of this house Is chic and interesting. Great collection of books. Bring ..."…"

Reviewed on Jul 6, 2020

Woodstock Historic Artist Estate - The Cottage House
Beautiful, Tranquil Woodstock Mountain House With Hot Tub and Ping Pong
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Situated in a rural location, this historic vacation home is within 3 mi (5 km) of Woodstock Public Library, Woodstock Golf Club, and Overlook Mountain Trailhead. ...

4.9/5Exceptional! (79 reviews)
Great property

"Great location; private yet convenient"…"

Reviewed on Oct 21, 2020

Beautiful, Tranquil Woodstock Mountain House With Hot Tub and Ping Pong
Mountain MOD Sleeps 10, 1 Mi to Town, Heated Pool to Sep. 30, Fireplace
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Situated in Woodstock, this vacation home is 1.4 mi (2.2 km) from Woodstock Public Library and 1.4 mi (2.3 km) from Woodstock Golf Club. Overlook Mountain Trailhead ...

5/5Exceptional! (5 reviews)
Great home

"Really nice, large home with mid century modern decor."…"

Reviewed on Mar 5, 2020

Mountain MOD Sleeps 10, 1 Mi to Town, Heated Pool to Sep. 30, Fireplace
Woodstock Mediterranean Retreat
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Situated in Woodstock, this vacation home is within 3 mi (5 km) of Woodstock Golf Club, Thorn Preserve - Catskill Center, and Woodstock Public Library. Ashokan ...

4.7/5Exceptional! (17 reviews)
Great stay

"Great stay at the home. Perfect location to town. Hard to find kitchen light but texted and got answer right away."…"

Reviewed on Jan 16, 2020

Woodstock Mediterranean Retreat
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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.

Other property types in Woodstock

The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

3 out of 5
48 Tannery Brook Rd, Woodstock, NY
The price is $155 per night from Nov 3 to Nov 4
4.4/5Wonderful! (65 reviews)

"Property was nice and proximity to Main Street was ideal. Could have used more supplies such as bar soap, hand sanitizer. Pocket door to bathroom was sketchy and was annoying to open and close."…"

Reviewed on Aug 30, 2020

The Woodstock Inn on the Millstream
Twin Gables of Woodstock

Twin Gables of Woodstock

2.5 out of 5
73 Tinker St, Woodstock, NY
The price is $149 per night from Oct 26 to Oct 27
4.8/5Exceptional! (5 reviews)

"The staff went above and beyond making us feel welcome and at home! Very clean, cozy, and a very short walk to all of the best Woodstock shopping, restaurants, and bars."…"

Reviewed on Oct 19, 2020

Twin Gables of Woodstock
Hotel Woodstock - Queen Anne's Lace Suite

Hotel Woodstock - Queen Anne's Lace Suite

Woodstock, NY
The price is $59 per night from Oct 29 to Oct 30
4.7/5Exceptional! (15 reviews)
Cool hotel in the center of town

"This hotel is old, small + very vibey..with all the important details, good hot water, comfy bed + downstairs is the best food, lattes in Woodstock! There's a small outdoor porch off the room that looks out at the mountains for morning coffee and the room is super quiet, we're already planning the ..."…"

Reviewed on Oct 25, 2019

Hotel Woodstock - Queen Anne's Lace Suite
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.