Woodstock Vacation Rentals

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Vacation Rentals in Woodstock

Hotel Woodstock - Daisy Suite

Hotel Woodstock - Daisy Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.9/5 Exceptional! (19 reviews)
"The town of Woodstock has it’s own unique charm. The Woodstock Hotel had all of the same charm in every nook and cranny in this VRBO! We will be back for a longer stay!!!"

Reviewed on Oct 17, 2021

Hotel Woodstock - Daisy Suite
Hotel Woodstock - Iris Suite

Hotel Woodstock - Iris Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (24 reviews)
Great place and excellent location!
"This room was perfect, right in town and close to Bearsville Theatre where we came to see a show."

Reviewed on Sep 28, 2021

Hotel Woodstock - Iris Suite
Hotel Woodstock - Dandelion Suite

Hotel Woodstock - Dandelion Suite

Woodstock, NY
The price is $99 per night from Oct 28 to Oct 28
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (13 reviews)
Perfection in Woodstock!
"The beautiful Dandelion suite/apt. at Hotel Woodstock surpassed our expections! Seamless check-in; gracious, kind and incredibly responsive host Dave; Beautiful rooms, spacious windowed kitchen, bedroom and living/guest room; lovely, tasteful and comfortable bedding. Just amazing! Highly recommend ..."

Reviewed on Aug 14, 2021

Hotel Woodstock - Dandelion Suite
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'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY

Woodstock, NY
The price is $165 per night from Oct 24 to Oct 24
Situated on a lake, this cabin is within a 10-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and Karma Triyana ...
3.8/5 Good! (17 reviews)
Simple and calm
"Nice land, very pretty and calm. Cabin was adorable and cozy. We would love to visit again."

Reviewed on Jun 27, 2021

'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Woodstock, NY
The price is $225 per night from Oct 25 to Oct 25
Situated on the waterfront, this romantic cottage is within 1 mi (2 km) of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (16 reviews)
Special little spot!
"I plan on staying next time I am in the area. Quiet except for the river! Full of character as well!"

Reviewed on Oct 4, 2021

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Hotel Woodstock - Tiger Lilly Suite

Hotel Woodstock - Tiger Lilly Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (18 reviews)
"Expected to come back. Had a lot of fun. Place was clean"

Reviewed on Aug 4, 2021

Hotel Woodstock - Tiger Lilly Suite
Hotel Woodstock - Aster Suite

Hotel Woodstock - Aster Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (13 reviews)
"Very quaint, and convenient."

Reviewed on Sep 20, 2021

Hotel Woodstock - Aster Suite
Hotel Woodstock - Sunflower Suite

Hotel Woodstock - Sunflower Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.7/5 Exceptional! (27 reviews)
Amazing Stay!!!
"This place was awesome drive there and park the car! Walking distance from everything. Place was super clean beds and pillows were very very comfortable. Extra linens at your disposal and kitchen was stocked with dishes and utensils. Will definitely be back to stay! Thanks again!!"

Reviewed on Sep 19, 2021

Hotel Woodstock - Sunflower Suite
Hotel Woodstock - Starflower Suite

Hotel Woodstock - Starflower Suite

Woodstock, NY
The price is $99 per night from Oct 25 to Oct 25
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (23 reviews)
great
"it was great. thank you. easy and super communicative and helpful."

Reviewed on Sep 10, 2021

Hotel Woodstock - Starflower Suite
Magical Chalet with spectacular views

Magical Chalet with spectacular views

Woodstock, NY
This family-friendly Woodstock chalet is located on a lake, within 2 mi (3 km) of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead ...
4.9/5 Exceptional! (38 reviews)
Family Reunion
"A beautiful place to stay and have fun with family and grandchild! The property manager was ultra responsive and nice!"

Reviewed on Sep 7, 2021

Magical Chalet with spectacular views
Hike Romantic Woodstock Mountaintop Studio🍁🍂🍃<br> May-Oct<br>Pool Deck Grill<br><br>

Hike Romantic Woodstock Mountaintop Studio🍁🍂🍃<br> May-Oct<br>Pool Deck Grill<br><br>

Woodstock, NY
Located in the mountains, this Woodstock apartment building offers ski-in/ski-out access within 3 mi (5 km) of Woodstock Public Library and Woodstock Golf Club ...
4.9/5 Exceptional! (33 reviews)
Beautiful Setting
"Cozy studio in a lovely setting. It was wonderful to get up in the morning and sit on the terrace taking in the beautiful view before heading into Woodstock and returning in the evening to relax with a glass of wine and watch the sky change colors."

Reviewed on Oct 1, 2021

Hike Romantic Woodstock Mountaintop Studio🍁🍂🍃<br> May-Oct<br>Pool Deck Grill<br><br>
Mountain Gardens - DOGS WELCOME<br>POOL OPEN until October!!!<br>Complete Privacy<br>

Mountain Gardens - DOGS WELCOME<br>POOL OPEN until October!!!<br>Complete Privacy<br>

Woodstock, NY
Located in the heart of Woodstock, this cottage is within 6 mi (10 km) of Platte Clove Preserve - Catskill Center, Woodstock Public Library, and Woodstock Golf ...
4.7/5 Exceptional! (44 reviews)
A Lovely Stay!
"Couldn't have asked for a nicer host or a more lovely cottage. The place was clean and tidy, every detail was thought of. Carol spoiled us and our dog, Rooster, and we were so appreciative. The location felt remote, tucked just below Lookout Mountain, but was a quick enough drive into Woodstock. ..."

Reviewed on Oct 6, 2021

Mountain Gardens - DOGS WELCOME<br>POOL OPEN until October!!!<br>Complete Privacy<br>
Hotel Woodstock - Queen Anne's Lace Suite

Hotel Woodstock - Queen Anne's Lace Suite

Woodstock, NY
The price is $99 per night from Nov 2 to Nov 2
Situated in Woodstock, this apartment building is within a 15-minute walk of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and ...
4.8/5 Exceptional! (33 reviews)
Gr8
"Super great. Easy. Affordable."

Reviewed on Aug 31, 2021

Hotel Woodstock - Queen Anne's Lace Suite
LIFE  ABOVE   1200’

LIFE ABOVE 1200’

Woodstock, NY
Situated in the mountains, this historic cabin is 2.2 mi (3.5 km) from Woodstock Public Library and 2.2 mi (3.6 km) from Woodstock Golf Club. Ashokan Rail Trail- ...
5/5 Exceptional! (5 reviews)
Great location
"We really enjoyed the private wooded location. The house was very comfortable and had great character. Fall colors were spectacular . Thirza was great to work with."

Reviewed on Oct 13, 2019

LIFE ABOVE 1200’
Beautiful, Tranquil Woodstock Mountain House with Hot Tub and Ping Pong

Beautiful, Tranquil Woodstock Mountain House with Hot Tub and Ping Pong

Woodstock, NY
This family-friendly Woodstock vacation home is located in a rural location, within 3 mi (5 km) of Woodstock Public Library, Woodstock Golf Club and Overlook ...
4.9/5 Exceptional! (102 reviews)
Woodstock Girls Weekend
"We arrived after dark and initially thought we were entering a horror movie driving into the dark woods. Til we saw how beautiful the house was! The house was more beautiful than the photos. Everything we could neee was there. The hot tub was amazing after a long day shopping and walking. The beds ..."

Reviewed on Sep 23, 2021

Beautiful, Tranquil Woodstock Mountain House with Hot Tub and Ping Pong
Plum Guide - Aquarian Exposition

Plum Guide - Aquarian Exposition

3.5 out of 5
23 Laura Lane, Woodstock, NY
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 ...
Plum Guide - Aquarian Exposition
NEW SUMMER DATES - Spend this time in the heart of Woodstock (Private Woods!)

NEW SUMMER DATES - Spend this time in the heart of Woodstock (Private Woods!)

Woodstock, NY
This family-friendly Woodstock vacation home is within 2 mi (3 km) of Woodstock Golf Club and Woodstock Public Library. Thorn Preserve - Catskill Center and ...
4.9/5 Exceptional! (81 reviews)
Wonderful House in the Woods(tock)
"Everything about this trip was fantastic - the house is beautiful and located on a gorgeous piece of property in the woods. The house was meticulously cleaned and cared for with plenty of space inside and outside. We really enjoyed the piano and electronic drum set, outside deck, and large kitchen ..."

Reviewed on Oct 20, 2021

NEW SUMMER DATES - Spend this time in the heart of Woodstock (Private Woods!)
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

Woodstock, NY
Situated in a rural location, this historic vacation home is 1.5 mi (2.4 km) from Woodstock Public Library and 1.5 mi (2.4 km) from Woodstock Golf Club. Overlook ...
4.8/5 Exceptional! (28 reviews)
Heavenly Place
"This is definitely one of our newest finds. Loved this home and all the accommodations..great for relaxing stay. Loved pool and the fact it's heated is a plus. If I could add anything is that it would be nice to have lights by the pool for night swimming. We went out and bought some battery led lanterns ..."

Reviewed on Oct 4, 2021

COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!
Plum Guide - Upstate Escape

Plum Guide - Upstate Escape

3.5 out of 5
13 Snow Ridge, Woodstock, NY
Situated in Woodstock, this vacation home is 0.8 mi (1.3 km) from Woodstock Golf Club and within 3 mi (5 km) of Woodstock Public Library and Thorn Preserve - ...
Plum Guide - Upstate Escape
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Woodstock, NY
This family-friendly Woodstock cottage is within 2 mi (3 km) of Woodstock Public Library and Woodstock Golf Club. Overlook Mountain Trailhead and Karma Triyana ...
4.9/5 Exceptional! (40 reviews)
Cozy cabin with a great location!
"A friend and I stayed in this cozy cabin for a weekend wedding celebration. The property is great! Just a short walk to town, but far enough away to feel very private. The rooms and facilities were charming and well maintained. Robyn was very helpful and a great hostess!"

Reviewed on Oct 14, 2021

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
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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.

Large Group Cabins Woodstock

'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY

Woodstock, NY
The price is $165 per night from Oct 24 to Oct 24
'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY
LIFE  ABOVE   1200’

LIFE ABOVE 1200’

Woodstock, NY
LIFE ABOVE 1200’
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.

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on … and on. 

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Woodstock vacation rentals range between $99 per night and $225 per night.

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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