Woodstock Vacation Rentals

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Vacation Rentals in Woodstock

Interior
A charming 1820's farmhouse

A charming 1820's farmhouse

Woodstock
10.0 out of 10, Exceptional, (29)
"Excellent accommodations! One of the best VRBO’s I’ve ever stayed in. There were 5 women traveling together for a long weekend and Carmen’s place was just the ticket with our own bedrooms and en suite bathrooms. We had the entire place to ourselves and felt very spoiled."
United States
kelly f.
$1,269 nightly
The price is $1,399
Dec 8 - Dec 9
Total with taxes and fees
A charming 1820's farmhouse
Condo, 2 Bedrooms | Dining
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
$566 nightly
The price is $631
Dec 9 - Dec 10
Total with taxes and fees
The Woods by Killington Vacation Rentals - 2 Bedrooms
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
$488 nightly
The price is $546
Dec 7 - Dec 8
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Interior
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, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$316 nightly
The price is $345
Dec 8 - Dec 9
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

2.0 star property
Killington
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
$415 nightly
The price is $469
Dec 8 - Dec 9
Total with taxes and fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Indoor pool, a heated pool
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

2.0 star property
The Woods
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
$380 nightly
The price is $429
Dec 6 - Dec 7
Total with taxes and fees
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Exterior
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
$171 nightly
The price is $187
Dec 10 - Dec 11
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Interior
Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse

Hartford
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
$180 nightly
The price is $203
Dec 11 - Dec 12
Total with taxes and fees
Addie's Place: A Quiet and Quirky Private Guesthouse
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking

3.0 star property
Ludlow
$333 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ludlow Ski Cabin 2 Mi to Ski Parking
Fridge, microwave, oven, stovetop
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
Mendon
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
$377 nightly
The price is $422
Dec 9 - Dec 10
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

The Suites at Killington Center

3.5 star property
Killington
$310 nightly
The price is $341
Dec 9 - Dec 10
Total with taxes and fees
The Suites at Killington Center
Condo, 2 Bedrooms | Sauna
Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo

3.5 star property
Killington
10.0 out of 10, Exceptional, (1)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
$507 nightly
The price is $564
Dec 8 - Dec 9
Total with taxes and fees
Fall Line Condo D4 2 Bedroom Condo
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

2.5 star property
Rutland
10.0 out of 10, Exceptional, (2)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
$172 nightly
The price is $193
Dec 7 - Dec 8
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!

Sharon
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
$233 nightly
The price is $261
Dec 8 - Dec 9
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Indoor pool, a heated pool
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

3.0 star property
The Woods
9.8 out of 10, Exceptional, (6)
"Very clean and well equipped condo! We enjoyed our stay."
United States
Tanya W.
$412 nightly
The price is $465
Dec 8 - Dec 9
Total with taxes and fees
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
Fridge, microwave, oven, stovetop
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
$456 nightly
The price is $511
Dec 7 - Dec 8
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Interior
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
$215 nightly
The price is $244
Dec 8 - Dec 9
Total with taxes and fees
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Exterior detail
Ben & Jerry Suite | Skiing | Hiking | Biking

Ben & Jerry Suite | Skiing | Hiking | Biking

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
$189 nightly
The price is $207
Dec 9 - Dec 10
Total with taxes and fees
Ben & Jerry Suite | Skiing | Hiking | Biking
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

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$230 nightly
The price is $260
Dec 6 - Dec 7
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Exterior
Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
9.8 out of 10, Exceptional, (43)
"The accommodations were great with plenty of room. We all wanted to lay on the living room couches because they were so comfortable! The property was nice and peaceful with lots of flowers, bushes and trees to observe."
United States
Karen P.
$417 nightly
The price is $467
Dec 7 - Dec 8
Total with taxes and fees
Spacious country home, beautiful sunsets, 40 acres
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
"Nice amenities, clean room, welcoming staff. Only 2 min drive from the Snowshed lodge. The on-site brewery and restaurant are pretty great."
Dmitriy 3-night trip
Posted 8 hours 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 $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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This vacation home rental outside of Woodstock is located in the city center and has a fireplace, a patio, and laundry facilities 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. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Woodstock?

Expedia has 30 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 Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, VINS Nature Center and Saskadena Six Ski Area are other places worth a visit.

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.