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Woodstock Vacation Rentals

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Dec 5 - Dec 6
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Dec 6 - Dec 7
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Woodstock

Private kitchen
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Woodstock
8.4 out of 10, Very Good, (9)
"Great place. Great location "
United States
Anonymous traveler
The price is ￥13,962
￥43,784 total
includes taxes & fees
Dec 15 - Dec 16
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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.
The price is ￥27,914
￥47,069 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

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
The price is ￥30,871
￥60,116 total
includes taxes & fees
Dec 13 - Dec 14
Streamside Cottage Half Mile to Town of Woodstock
Outdoor dining
Fall Foliage Getaway!

Fall Foliage Getaway!

Woodstock
10.0 out of 10, Exceptional, (12)
"We loved the place - beautiful house and setting."
United States
Michele P.
The price is ￥52,744
￥116,062 total
includes taxes & fees
Dec 7 - Dec 8
Fall Foliage Getaway!
Outdoor pool
Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House

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.
The price is ￥85,027
￥147,005 total
includes taxes & fees
Dec 7 - Dec 8
Woodstock Historic Artist Estate - The Museum House
1 bedroom, WiFi, bed sheets
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

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.
The price is ￥25,619
￥56,311 total
includes taxes & fees
Dec 7 - Dec 8
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
Exterior
Starlite Motel

Starlite Motel

2.5 star property
Big Indian
9.2 out of 10, Wonderful, (273)
"Awesome place to stay!"
United States
Earl
The price is ￥19,152
￥21,450 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Starlite Motel
Dining
Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access

Saugerties
10.0 out of 10, Exceptional, (13)
"Lovely home! Easy check in and in a quiet area. "
United States
Rachel B.
The price is ￥13,155
￥42,366 total
includes taxes & fees
Dec 17 - Dec 18
Peaceful Cabin w/ Fire Pit & Creek Access
Property grounds
Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck

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
The price is ￥13,682
￥37,240 total
includes taxes & fees
Dec 8 - Dec 9
Private Studio Close to Downtown Rhinebeck
Property grounds
Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

Stone Ridge
9.4 out of 10, Exceptional, (14)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥11,631
￥26,736 total
includes taxes & fees
Dec 11 - Dec 12
Cozy Apartment with Sauna in Historic Stone Ridge
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!

Kingston
9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
The price is ￥11,480
￥44,306 total
includes taxes & fees
Dec 10 - Dec 11
Retro Retreat: renovated 2BR, desk, no chore list!
Exterior
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥13,264
￥22,702 total
includes taxes & fees
Dec 7 - Dec 8
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Fridge, microwave, oven, stovetop
Higashi: New Paltz family home with King bed minutes to downtown

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

New Paltz
9.8 out of 10, Exceptional, (20)
"Great place to stay! We enjoyed our time here. "
United States
Christy B.
The price is ￥16,433
￥50,202 total
includes taxes & fees
Dec 18 - Dec 19
Higashi: New Paltz family home with King bed minutes to downtown
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥11,635
￥39,267 total
includes taxes & fees
Dec 14 - Dec 15
Campfire Cottage: Fireplace, fire pit & no chores!
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is ￥13,259
￥36,561 total
includes taxes & fees
Dec 9 - Dec 10
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown
10.0 out of 10, Exceptional, (5)
"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.
The price is ￥16,909
￥33,185 total
includes taxes & fees
Dec 14 - Dec 15
Charming loft cottage in tranquil Germantown with WiFi, AC
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very Good, (33)
"Perfect location. Easy access to great surrounding area. Nice space. We had only one night. Wish it was longer!"
United States
loretta p.
The price is ￥17,447
￥41,599 total
includes taxes & fees
Dec 11 - Dec 12
The Studio at the Inn at High Falls
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.

Saugerties
10.0 out of 10, Exceptional, (12)
"Cozy and beautiful house. "
United States
Seung L.
The price is ￥15,358
￥27,626 total
includes taxes & fees
Dec 7 - Dec 8
Country Cottage with beautiful views and easy access to Catskills activities.
Terrace/patio
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

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.
The price is ￥12,561
￥34,564 total
includes taxes & fees
Dec 11 - Dec 12
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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
"Yes to all questions!!"
Mary 1-night trip
Posted 19 hours ago
Beekman Arms Hotel

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

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Look no further and take a look at our great range of rental properties in Woodstock!

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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.