Holiday Rentals in Woodstock

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Our top choices for Woodstock holiday rentals

10.0 out of 10, Exceptional, (6 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is €169
includes taxes & fees
1 Mar - 2 Mar
Addie's Place: A Quiet and Quirky Guesthouse
10.0 out of 10, Exceptional, (7 reviews)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is €246
includes taxes & fees
4 Mar - 5 Mar
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
9.6 out of 10, Exceptional, (15 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
The price is €161
includes taxes & fees
16 Mar - 17 Mar
Treehouse at Wise Pines- NoBo
10.0 out of 10, Exceptional, (14 reviews)
"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "
United States
Adam B.
The price is €293
includes taxes & fees
24 Mar - 25 Mar
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Condo resort in Killington

Mountain Green
2.0 star property
7.2 out of 10, Good, (20 reviews)
"Great !"
United States
Raul
The price is €231
includes taxes & fees
11 Mar - 12 Mar
Mountain Green
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €262
includes taxes & fees
11 Mar - 12 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
10.0 out of 10, Exceptional, (20 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
The price is €499
includes taxes & fees
3 Mar - 4 Mar
Charming Lakefront Cottage on Lake Mascoma
9.6 out of 10, Exceptional, (11 reviews)
"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.
The price is €165
includes taxes & fees
11 Mar - 12 Mar
Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
9.2 out of 10, Wonderful, (28 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.
The price is €360
includes taxes & fees
28 Mar - 29 Mar
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
8.4 out of 10, Very good, (36 reviews)
"Great stay!"
United States
Bryann F.
The price is €260
includes taxes & fees
2 Mar - 3 Mar
Comfortable mountain gem with pool, mountain views, & indoor parking space
10.0 out of 10, Exceptional, (11 reviews)
"perfect setup, very clean and comfortable. "
United States
Jeremiah J.
The price is €360
includes taxes & fees
2 Mar - 3 Mar
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
9.4 out of 10, Exceptional, (69 reviews)
"Great little condo, near everything and 2 min drive to K1 Lodge. "
United States
zina r.
The price is €271
includes taxes & fees
1 Mar - 2 Mar
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
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.
The price is €238
includes taxes & fees
8 Mar - 9 Mar
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is €198
includes taxes & fees
10 Mar - 11 Mar
Efficient condo near slopes with kitchenette & great location

Apartment in Rutland

Cozy Rutland Retreat
9.8 out of 10, Exceptional, (6 reviews)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
The price is €170
includes taxes & fees
23 Mar - 24 Mar
Cozy Rutland Retreat
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is €275
includes taxes & fees
24 Mar - 25 Mar
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
The price is €317
includes taxes & fees
24 Mar - 25 Mar
Luxury Condo Tucked in the Heart of Killington
10.0 out of 10, Exceptional, (14 reviews)
"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
The price is €322
includes taxes & fees
10 Mar - 11 Mar
Jack S`Bearo - Slopes, Fireplace, Pool.
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is €169
includes taxes & fees
10 Mar - 11 Mar
Vermont Suite | 10 Min to Killington & Woodstock
9.6 out of 10, Exceptional, (4 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is €270
includes taxes & fees
2 Mar - 3 Mar
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
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, apart-hotels, 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 favorite 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 depends 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 €165 per night. Entering your travel dates in the search wizard you might find 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. 

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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?

Spectacular opportunity to enjoy the finest property in Killington Summit: This holiday home rental outside of Woodstock is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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.