Woodstock Vacation Rentals

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Our top choices for Woodstock vacation rentals

9.8 out of 10, Exceptional, (25 reviews)
"Friendly owners with a very comfortable and accommodating space.Very well thought out with a great common space .Hiking trails , fire pit , animals , fresh eggs and produce in season.Highly recommended!!"
United States
Jo-Alice S.
$172 nightly
The price is $188
Mar 16 - Mar 17
Total with taxes and fees
Treehouse at Wise Pines- SoBo
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.
$236 nightly
The price is $264
Mar 16 - Mar 17
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
10.0 out of 10, Exceptional, (8 reviews)
"Perfect size and location! "
United States
Lyn H.
$195 nightly
The price is $220
Mar 23 - Mar 24
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$277 nightly
The price is $313
Apr 13 - Apr 14
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
10.0 out of 10, Exceptional, (15 reviews)
"Hot tub was wonderful! We only opened it half way for the two of us and it maintained 102-103 the entire time and was very clean! "
United States
Crissi C.
$288 nightly
The price is $314
Apr 13 - Apr 14
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
$248 nightly
The price is $280
Apr 9 - Apr 10
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
10.0 out of 10, Exceptional, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
$265 nightly
The price is $297
Mar 17 - Mar 18
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Apartment in Rutland

Cozy Rutland Retreat
9.8 out of 10, Exceptional, (6 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
$168 nightly
The price is $188
Mar 15 - Mar 16
Total with taxes and fees
Cozy Rutland Retreat
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
$199 nightly
The price is $218
Apr 14 - Apr 15
Total with taxes and fees
Vermont Suite | 10 Min to Woodstock & Killington
9.2 out of 10, Wonderful, (29 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
$219 nightly
The price is $247
Apr 13 - Apr 14
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.6 out of 10, Exceptional, (4 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
9.0 out of 10, Wonderful, (25 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
$237 nightly
The price is $268
Mar 19 - Mar 20
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.0 out of 10, Wonderful, (6 reviews)
"We did a quick ski getaway, great place, and close to the mountain!"
United States
Al Z.
$270 nightly
The price is $305
Mar 18 - Mar 19
Total with taxes and fees
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
8.4 out of 10, Very Good, (36 reviews)
"Great stay!"
United States
Bryann F.
$264 nightly
The price is $298
Apr 14 - Apr 15
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space
9.8 out of 10, Exceptional, (11 reviews)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
$576 nightly
The price is $646
Mar 15 - Mar 16
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
7.0 out of 10, Good, (47 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
$224 nightly
The price is $253
Mar 18 - Mar 19
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts
10.0 out of 10, Exceptional, (21 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
$564 nightly
The price is $612
Mar 15 - Mar 16
Total with taxes and fees
Charming Lakefront Cottage on Lake Mascoma

Condo resort in Killington

Mountain Green
2.0 star property
7.4 out of 10, Good, (21 reviews)
"Older unit but very convenient for the slopes, and nice to have a bar/grill in the building."
United States
Neil
$227 nightly
The price is $250
Apr 7 - Apr 8
Total with taxes and fees
Mountain Green
10.0 out of 10, Exceptional, (14 reviews)
"Great place to lay your head in between days on the mountain. The hosts Holly and Dan are so nice. "
United States
Carly C.
$268 nightly
The price is $302
Mar 17 - Mar 18
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool.
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

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 $220 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.

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?

Idyllic Lakefront House Suited Two Families: This vacation home rental outside of Woodstock is located on a lake and has a fireplace, a patio, 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 31 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, Union Arena Community 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.