Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Woodstock vacation rentals

Interior
A charming 1820's farmhouse

A charming 1820's farmhouse

A charming 1820's farmhouse
Woodstock
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.
$1,316 nightly
The price is $1,452
Jan 6 - Jan 7
Total with taxes and fees
A charming 1820's farmhouse
Property grounds
Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
$84 nightly
The price is $94
Jan 4 - Jan 5
Total with taxes and fees
Off Grid Glamping Shed with River Access
Exterior
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
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
$171 nightly
The price is $187
Jan 7 - Jan 8
Total with taxes and fees
Treehouse at Wise Pines- NoBo
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.2 out of 10, Wonderful, (5)
$172 nightly
The price is $193
Jan 5 - Jan 6
Total with taxes and fees
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Property grounds
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (4)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
$252 nightly
The price is $282
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 | Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
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
$676 nightly
The price is $760
Jan 5 - Jan 6
Total with taxes and fees
The Woods by Killington Vacation Rentals - 2 Bedrooms
TV, DVD player, books
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
$293 nightly
The price is $331
Jan 7 - Jan 8
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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (75)
"Perfect location for a quick ski trip. "
United States
Michael D.
$283 nightly
The price is $320
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

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
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.
$268 nightly
The price is $303
Jan 5 - Jan 6
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Interior
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
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.
$236 nightly
The price is $264
Jan 4 - Jan 5
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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$368 nightly
The price is $403
Jan 12 - Jan 13
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
Killington Studio: Great Location! Comfy. 431

Killington Studio: Great Location! Comfy. 431

Killington Studio: Great Location! Comfy. 431
Killington
8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
$239 nightly
The price is $270
Jan 4 - Jan 5
Total with taxes and fees
Killington Studio: Great Location! Comfy. 431
Property grounds
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
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.
$533 nightly
The price is $597
Jan 5 - Jan 6
Total with taxes and fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Killington
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.
$243 nightly
The price is $275
Jan 4 - Jan 5
Total with taxes and fees
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Exterior detail
Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
$211 nightly
The price is $231
Jan 19 - Jan 20
Total with taxes and fees
Ben & Jerry’s Studio | 10 Min to Killington
Condo, 1 Bedroom | Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
$334 nightly
The price is $377
Jan 4 - Jan 5
Total with taxes and fees
Killington Ski Resort VT Vacation Condos
Smart TV, fireplace
Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
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
$341 nightly
The price is $385
Jan 14 - Jan 15
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool.
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
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 6 - Jan 7
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Fridge, microwave, oven, stovetop
Wade`s World Ski Home FirePlace Shuttle location

Wade`s World Ski Home FirePlace Shuttle location

Wade`s World Ski Home FirePlace Shuttle location
2.0 star property
Killington
9.6 out of 10, Exceptional, (5)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
$366 nightly
The price is $413
Jan 14 - Jan 15
Total with taxes and fees
Wade`s World Ski Home FirePlace Shuttle location
Terrace/patio
Killington condo 5 min to killington resort

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
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.
$343 nightly
The price is $388
Feb 3 - Feb 4
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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"Front desk clerk was very welcoming and made us aware of all the special service you offer. (Example: the times the breakfast buffet opens, the hours of the bar etc.)"
BETH 1-night trip
Posted 2 days ago
Hilton Garden Inn Hanover Lebanon

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 $187 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.