Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Woodstock vacation rentals

Interior

A charming 1820's farmhouse

A charming 1820's farmhouse
Woodstock
10.0 out of 10, Exceptional, (30 reviews)
"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 23 - Jan 24
Total with taxes and fees
A charming 1820's farmhouse
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 reviews)
"Perfect size and location! "
United States
Lyn H.
$167 nightly
The price is $189
Jan 21 - Jan 22
Total with taxes and fees
Addie's Place: A Quiet and Quirky Private Guesthouse
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.8 out of 10, Exceptional, (14 reviews)
"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 21 - Jan 22
Total with taxes and fees
Treehouse at Wise Pines- NoBo
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, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$303 nightly
The price is $330
Jan 21 - Jan 22
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Condo, 2 Bedrooms | Interior

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 review)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
Fall Line Condo D4 2 Bedroom Condo
Terrace/patio

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, (6 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
$255 nightly
The price is $285
Jan 21 - Jan 22
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

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
9.6 out of 10, Exceptional, (7 reviews)
$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
Exterior

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 reviews)
"Great property, as advertised."
United States
Chris A.
$289 nightly
The price is $327
Jan 25 - Jan 26
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Private kitchen

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 reviews)
"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.
$325 nightly
The price is $364
Jan 22 - Jan 23
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (78 reviews)
"Very nice condo - not large but very convenient. Everything is good quality - dishes, bed linens. Plenty of electrical and USB outlets everywhere, dedicated WiFi in the unit. Kitchen was fully stocked with supplies. 5 min drive to Okemo, 3 min to Shaw supermarket. Ample parking"
United States
Valentin
$232 nightly
The price is $262
Jan 21 - Jan 22
Total with taxes and fees
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Fridge, microwave, oven, stovetop

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

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (10 reviews)
"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.
$503 nightly
The price is $563
Jan 22 - Jan 23
Total with taxes and fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$338 nightly
The price is $372
Feb 2 - Feb 3
Total with taxes and fees
The Suites at Killington Center
Smart TV, fireplace

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 reviews)
"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.
$404 nightly
The price is $456
Jan 21 - Jan 22
Total with taxes and fees
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Exterior

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 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
$594 nightly
The price is $665
Feb 9 - Feb 10
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Condo, 2 Bedrooms | Living area

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 reviews)
"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
Interior

Killington Bill Condo w/ Kitchenette Sleeps 4

Killington Bill Condo w/ Kitchenette Sleeps 4
Killington
9.4 out of 10, Exceptional, (13 reviews)
"Great stay, clean and convenient location. Bed was not the most comfortable though."
United States
Haaser21
Killington Bill Condo w/ Kitchenette Sleeps 4
Exterior

Ski You Later, Alligator Condo with Mountain Views on Shuttle Route

Ski You Later, Alligator Condo with Mountain Views on Shuttle Route
Killington
9.6 out of 10, Exceptional, (8 reviews)
"Cozy"
United States
Vito F.
Ski You Later, Alligator Condo with Mountain Views on Shuttle Route
3 bedrooms, desk, iron/ironing board, travel crib

Blueberry Hill Escape | Pet Friendly | HotTub | AC

Blueberry Hill Escape | Pet Friendly | HotTub | AC
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
$503 nightly
The price is $563
Jan 21 - Jan 22
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | AC
Exterior

Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.0 out of 10, Wonderful, (4 reviews)
"This place is a perfect rustic getaway with easy convenience to town. The host was great. Spacious and super relaxing with nice view out back. "
United States
Thaddeus T.
$391 nightly
The price is $395
Feb 1 - Feb 2
Total with taxes and fees
Killington Retreat | Deck-Fire Pit-Mountain Views!
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Amazing place! "
United States
Tara
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski 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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Awesome customer service- great room"
Katrina 1-night trip
Posted 1 day ago
North Star Lodge and Resort

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 $193 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 Red Wagon Toy Company, 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental outside of Woodstock is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.