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Woodstock Vacation Rentals

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In two weeks
Dec 19 - Dec 21
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Jan 30 - Feb 1
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Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Woodstock

Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Cottage in Woodstock

10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cottage in woodstock

9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$276 nightly
The price is $309
Dec 14 - Dec 15
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Vacation Home in Woodstock

10.0 out of 10, Exceptional, (116)
"great property with lots of play/sleep/eat options for a large family. Loved mornings and nights on the large screened porch---our favorite spot. nice proximity to the town of Woodstock ."
United States
Jo C.
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Exterior
Starlite Motel

Aparthotel in Big Indian

2.5 star property
9.2 out of 10, Wonderful, (273)
"Awesome place to stay!"
United States
Earl
$111 nightly
The price is $125
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlite Motel
Exterior
The Farm at Hyde Park

Vacation Home in Staatsburg

9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Cabin in Saugerties

8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Dec 10 - Dec 11
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Apartment in Saugerties

9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Vacation Home in Kingston

9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
$216 nightly
The price is $241
Dec 9 - Dec 10
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Terrace/patio
Hamptons on the Hudson in South Saugerties

Vacation Home in Glasco

10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Vacation Home in Bearsville

10.0 out of 10, Exceptional, (124)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Cottage in West Shokan

10.0 out of 10, Exceptional, (54)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Cabin in Saugerties

9.0 out of 10, Wonderful, (13)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
Outdoor dining
Mid-Century DJ’s Dream

Apartment in Staatsburg

10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
$174 nightly
The price is $197
Dec 11 - Dec 12
Total with taxes and fees
Mid-Century DJ’s Dream
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Cabin in Hunter

10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
$867 nightly
The price is $936
Dec 8 - Dec 9
Total with taxes and fees
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Smart TV, fireplace, DVD player, foosball
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Vacation Home in West Kill

9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

Vacation Home in Hunter

9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Apartment in Kingston

9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
$203 nightly
The price is $227
Dec 8 - Dec 9
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
$305 nightly
The price is $330
Dec 8 - Dec 9
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Dining
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Cabin in Grahamsville

9.4 out of 10, Exceptional, (36)
"Very well stocked. Beautiful, quiet location. Very comfortable. "
United States
Ladytiger
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Exterior
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

Condo in Hunter Highlands

10.0 out of 10, Exceptional, (10)
"We loved staying at this condo. The location was amazing for back and forth to the slopes it was so easy! The beds were so comfortable and the house was clean! Communication with the owner was excellent. We will definitely stay again! "
United States
Melissa B.
$1,183 nightly
The price is $1,278
Dec 8 - Dec 9
Total with taxes and fees
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
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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Top Woodstock Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"The staff was very freindly and helpful. I thought this place was a great value. Clean room. Breakfast was good. I took advantage of the fitness room which was nice to have. Good location, close to restaurants and a grocery store. "
Mark 1-night trip
Posted 2 days ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Woodstock

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 low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Woodstock?

Yes, there are vacation rentals close to well known attractions in Woodstock, or you can choose a more secluded option if you want a relaxing place to stay. The forests and art scene are just a few reasons why tourists like Woodstock. Make sure you have time to check out the riverfront and mountain views during your trip.

What's the top vacation rental in Woodstock?

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock: This highly rated vacation home rental in Woodstock is located near skiing and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Woodstock?

Expedia has 69 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Enjoy the outdoors at Overlook Mountain Trailhead and The Comeau Property, or simply take in cultural attractions like Colony and SweetHeart Gallery. Other places in town to visit include Woodstock Music Shop and Catskill State Park.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned properties you can reserve for several days or longer in Woodstock. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.