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Woodstock Vacation Rentals

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Dec 2 - Dec 3
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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.
$279 nightly
The price is $312
Dec 7 - Dec 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Private kitchen
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Apartment in Woodstock

8.4 out of 10, Very Good, (9)
"Great place. Great location "
United States
Anonymous traveler
$248 nightly
The price is $278
Dec 9 - Dec 10
Total with taxes and fees
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Outdoor dining
Fall Foliage Getaway!

Vacation Home in Woodstock

10.0 out of 10, Exceptional, (12)
"We loved the place - beautiful house and setting."
United States
Michele P.
$645 nightly
The price is $722
Dec 3 - Dec 4
Total with taxes and fees
Fall Foliage Getaway!
Outdoor pool
Woodstock Historic Artist Estate - The Museum House

Vacation Home in Woodstock

10.0 out of 10, Exceptional, (6)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
$855 nightly
The price is $958
Dec 3 - Dec 4
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
1 bedroom, WiFi, bed sheets
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Apartment in Woodstock

9.8 out of 10, Exceptional, (10)
"In the heart of woodstock, walking distance to any of the shops and restaurants, even grocery stores!! For the low price, it was a great place to stay, great quiet area and felt so safe!"
United States
Eden C.
$322 nightly
The price is $361
Dec 3 - Dec 4
Total with taxes and fees
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
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
$117 nightly
The price is $131
Dec 3 - Dec 4
Total with taxes and fees
Starlite Motel
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Germantown

10.0 out of 10, Exceptional, (4)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
$191 nightly
The price is $214
Dec 10 - Dec 11
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Outdoor dining
Jessie's Harvest House Suite

Chalet in Tannersville

10.0 out of 10, Exceptional, (2)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
$165 nightly
The price is $174
Dec 3 - Dec 4
Total with taxes and fees
Jessie's Harvest House Suite
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.
$211 nightly
The price is $236
Dec 4 - Dec 5
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Vacation Home in Kingston

10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$214 nightly
The price is $240
Dec 3 - Dec 4
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Saugerties

10.0 out of 10, Exceptional, (12)
"Cozy and beautiful house. "
United States
Seung L.
$159 nightly
The price is $178
Dec 3 - Dec 4
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
Dining
Peaceful Cabin w/ Fire Pit & Creek Access

Vacation Home in Saugerties

10.0 out of 10, Exceptional, (13)
"Lovely home! Easy check in and in a quiet area. "
United States
Rachel B.
$254 nightly
The price is $275
Dec 16 - Dec 17
Total with taxes and fees
Peaceful Cabin w/ Fire Pit & Creek Access
Fridge, microwave, oven, stovetop
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Chalet in Hunter

9.6 out of 10, Exceptional, (14)
"Beautiful location in a well kept property! Highly recommend it."
United States
Robert
$229 nightly
The price is $247
Dec 3 - Dec 4
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Property grounds
Private Studio Close to Downtown Rhinebeck

Apartment in RHINEBECK

10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
$193 nightly
The price is $218
Dec 3 - Dec 4
Total with taxes and fees
Private Studio Close to Downtown Rhinebeck
Pool
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Apartment in Hunter Highlands

9.8 out of 10, Exceptional, (6)
"Great stay! We will be back!"
United States
Michael
$198 nightly
The price is $215
Dec 10 - Dec 11
Total with taxes and fees
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
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 3 - Dec 4
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Apartment in Kingston

9.4 out of 10, Exceptional, (22)
"This was a great stay away, just for a couple of quiet days. Inside the house was excellent. "
United States
Dennis M.
$206 nightly
The price is $230
Dec 9 - Dec 10
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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 6 - Dec 7
Total with taxes and fees
Mid-Century DJ’s Dream
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

Beekman Arms Hotel

Beekman Arms Hotel

10/10 Excellent
"The general manager was warm and welcoming, our room was cozy and comfortable, and the inn was centrally located. We will definitely be back!"
Nancy 2-night trip
Posted 2 days ago
Beekman Arms Hotel

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 $131 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.