Woodstock Vacation Rentals

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In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Woodstock vacation rentals

Interior
A charming 1820's farmhouse

Vacation Home in Woodstock

A charming 1820's farmhouse
10.0 out of 10, Exceptional, (30)
"Beautiful home. It was a good location for my family to attend a family wedding at the Woodstock Inn."
United States
Robin H.
$1,330 nightly
The price is $1,468
Jan 11 - Jan 12
Total with taxes and fees
A charming 1820's farmhouse
Exterior
Off Grid Glamping Shed with River Access

Vacation Home in Randolph

Off Grid Glamping Shed with River Access
2.0 star property
10.0 out of 10, Exceptional, (1)
$84 nightly
The price is $94
Jan 8 - Jan 9
Total with taxes and fees
Off Grid Glamping Shed with River Access
Property grounds
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
$172 nightly
The price is $188
Jan 12 - Jan 13
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Property grounds
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.6 out of 10, Exceptional, (7)
$172 nightly
The price is $193
Jan 22 - Jan 23
Total with taxes and fees
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Terrace/patio
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (5)
"Cabin was spotless and exactly what I expected"
United States
mark g.
$247 nightly
The price is $276
Jan 13 - Jan 14
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Condo, 2 Bedrooms | Living area
The Woods by Killington Vacation Rentals - 2 Bedrooms

Condo in The Woods

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The Woods by Killington Vacation Rentals - 2 Bedrooms
Exterior
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Condo in Killington

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
$290 nightly
The price is $328
Jan 8 - Jan 9
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (75)
"Perfect location for a quick ski trip. "
United States
Michael D.
$276 nightly
The price is $312
Jan 11 - Jan 12
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Exterior
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Condo in Ludlow

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
$276 nightly
The price is $312
Jan 12 - Jan 13
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Private kitchen
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Vacation Home in Mendon

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
9.8 out of 10, Exceptional, (6)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
$225 nightly
The price is $252
Jan 8 - Jan 9
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$358 nightly
The price is $392
Jan 20 - Jan 21
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
Killington Studio: Great Location! Comfy. 431

Condo in Killington

Killington Studio: Great Location! Comfy. 431
8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
Killington Studio: Great Location! Comfy. 431
Fridge, microwave, oven, stovetop
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chalet in Chester

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
10.0 out of 10, Exceptional, (10)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Condo in Killington

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Property grounds
Ben & Jerry’s Studio | 10 Min to Killington

Apartment in Bridgewater

Ben & Jerry’s Studio | 10 Min to Killington
9.2 out of 10, Wonderful, (7)
"Overall, a great stay. "
United States
Meghan J.
$197 nightly
The price is $215
Jan 12 - Jan 13
Total with taxes and fees
Ben & Jerry’s Studio | 10 Min to Killington
Condo, 1 Bedroom | Exterior
Killington Ski Resort VT Vacation Condos

Condo in Killington

Killington Ski Resort VT Vacation Condos
3.5 star property
$371 nightly
The price is $419
Jan 21 - Jan 22
Total with taxes and fees
Killington Ski Resort VT Vacation Condos
Fridge, microwave, oven, stovetop
Jack S`Bearo - Slopes, Fireplace, Pool.

Apartment in Killington

Jack S`Bearo - Slopes, Fireplace, Pool.
10.0 out of 10, Exceptional, (13)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
$273 nightly
The price is $308
Jan 14 - Jan 15
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool.
TV
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Condo in Killington

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$277 nightly
The price is $313
Jan 12 - Jan 13
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Terrace/patio
Wade`s World Ski Home FirePlace Shuttle location

Apartment in Killington

Wade`s World Ski Home FirePlace Shuttle location
2.0 star property
9.6 out of 10, Exceptional, (5)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
$497 nightly
The price is $550
Jan 13 - Jan 14
Total with taxes and fees
Wade`s World Ski Home FirePlace Shuttle location
Living area
Killington condo 5 min to killington resort

Condo in Killington

Killington condo 5 min to killington resort
9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
$288 nightly
The price is $325
Jan 8 - Jan 9
Total with taxes and fees
Killington condo 5 min to killington resort
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The "
Stephen 2-night trip
Posted 1 day ago
The Mountain Inn at Killington

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 $188 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, we offer vacation rentals in Woodstock close to Billings Farm and Museum, or you can choose a more remote option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your vacation.

What's the top vacation rental that Woodstock has to offer?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This vacation home rental outside of Woodstock is located in the mountains and has an indoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware, and a coffee maker. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Woodstock?

Expedia has 28 vacation rentals for your stay in Woodstock.

What’s there to see and do in Woodstock?

Cultural attractions include Woodstock Town Hall Theatre and Billings Farm and Museum, whereas Marsh-Billings-Rockefeller National Historical Park and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Killington Resort and Okemo Mountain Resort.

What’s a vacation rental in Woodstock like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Woodstock. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.