Woodstock Holiday Rentals

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Our top choices for Woodstock holiday rentals

Holiday 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.
The price is AU$2,211
includes taxes & fees
3 Jan - 4 Jan 2026
A charming 1820's farmhouse
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$142
includes taxes & fees
30 Dec - 31 Dec
Off Grid Glamping Shed with River Access
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.
The price is AU$871
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
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
The price is AU$282
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse at Wise Pines- NoBo
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is AU$435
includes taxes & fees
13 Jan - 14 Jan 2026
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
9.2 out of 10, Wonderful, (5)
The price is AU$290
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is AU$397
includes taxes & fees
5 Jan - 6 Jan 2026
Woodstock Studio | 10 Min to Killington
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is AU$483
includes taxes & fees
11 Jan - 12 Jan 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is AU$629
includes taxes & fees
20 Jan - 21 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is AU$508
includes taxes & fees
7 Jan - 8 Jan 2026
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
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.
The price is AU$398
includes taxes & fees
19 Jan - 20 Jan 2026
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (17)
"Great communication from Jeff."
United States
Dennis
The price is AU$427
includes taxes & fees
12 Jan - 13 Jan 2026
Mountain Green
3.5 star property
The price is AU$630
includes taxes & fees
21 Jan - 22 Jan 2026
Killington Ski Resort VT Vacation Condos
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.
The price is AU$467
includes taxes & fees
5 Jan - 6 Jan 2026
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is AU$887
includes taxes & fees
5 Jan - 6 Jan 2026
Gnome Home Mountain Ski Chalet w/Sauna Killington
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is AU$860
includes taxes & fees
12 Jan - 13 Jan 2026
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AU$533
includes taxes & fees
12 Jan - 13 Jan 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
8.6 out of 10, Excellent, (14)
"Excellent Location.. "
United States
Juan Carlos L.
The price is AU$564
includes taxes & fees
26 Jan - 27 Jan 2026
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is AU$471
includes taxes & fees
4 Jan - 5 Jan 2026
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodstock holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as AU$282 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 holiday.

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 holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your holiday.

What are some of the best holiday rentals that Woodstock has to offer?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This holiday home rental outside of Woodstock is located in the mountains, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware and a coffee maker. You can relax into your holiday with a garden and 1 hot tub.

How many holiday rentals are there in Woodstock?

Expedia has 29 holiday 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, Saskadena Six Ski Area and Green Mountain National Forest are other places worth a visit.

What’s a holiday rental in Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.