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Woodstock Vacation Rentals

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Our top choices for Woodstock vacation rentals

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (17 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is CA $161
CA $253 total
includes taxes & fees
Nov 17 - Nov 18
Fat Sheep Farm & Cabins

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is CA $154
CA $280 total
includes taxes & fees
Nov 16 - Nov 17
Bridgewater Living - Ben&Jerry Suite

3. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is CA $308
CA $733 total
includes taxes & fees
Nov 17 - Nov 18
Pet Friendly | Game Room | Minutes to Woodstock and Killington

4. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $154
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
Bridgewater Living - Ski VT Suite

5. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (23 reviews)
"Perfect overnight accommodation for King Arthur baking classes!"
United States
beth k.
The price is CA $120
CA $235 total
includes taxes & fees
Nov 16 - Nov 17
Addie's Place: A Quiet and Quirky Guesthouse

6. 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, (16 reviews)
"Our stay in this tiny home was perfect! Very cozy and private. The host was very responsive and everything was exactly as described."
United States
Kat V.
The price is CA $188
CA $384 total
includes taxes & fees
Nov 16 - Nov 17
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

7. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is CA $399
CA $1,172 total
includes taxes & fees
Nov 16 - Nov 17
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

8. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is CA $118
CA $419 total
includes taxes & fees
Nov 18 - Nov 19
Mountain Green ground-floor condo with private yard off the patio

9. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.2 out of 10, Wonderful, (9 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is CA $402
CA $733 total
includes taxes & fees
Nov 16 - Nov 17
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

10. Adventure Cabin Hot Tub Sauna Trails Game Area

Adventure Cabin Hot Tub Sauna Trails Game Area
Cavendish
10.0 out of 10, Exceptional, (30 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
The price is CA $284
CA $581 total
includes taxes & fees
Nov 16 - Nov 17
Adventure Cabin Hot Tub Sauna Trails Game Area

11. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is CA $146
CA $467 total
includes taxes & fees
Nov 16 - Nov 17
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

12. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Worked for what we needed - host was responsive to all comments."
United States
Kristen O.
The price is CA $172
CA $675 total
includes taxes & fees
Nov 16 - Nov 17
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

13. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Clean and cozy. Perfect spot for racing the.VT Overland"
United States
Mike T.
The price is CA $120
CA $366 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Village Condo-Okemo Shuttle

14. 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, (5 reviews)
"Great room!"
United States
Carla M.
The price is CA $136
CA $486 total
includes taxes & fees
Nov 16 - Nov 17
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

15. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
United States
Nathan H.
The price is CA $136
CA $486 total
includes taxes & fees
Nov 16 - Nov 17
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

16. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (10 reviews)
"Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10. Highly recommend."
United States
Lisa
The price is CA $170
CA $691 total
includes taxes & fees
Nov 16 - Nov 17
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

17. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you
Chittenden
The price is CA $231
CA $507 total
includes taxes & fees
Nov 16 - Nov 17
Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

18. Modern Killington Farmhouse Condo: Close to it all! 412

Modern Killington Farmhouse Condo: Close to it all! 412
Killington
10.0 out of 10, Exceptional, (62 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
United States
Tyler L.
The price is CA $172
CA $647 total
includes taxes & fees
Nov 16 - Nov 17
Modern Killington Farmhouse Condo: Close to it all! 412

19. Trailside Village 5: Wood Stove, Private Sauna and Hot Tub

Trailside Village 5: Wood Stove, Private Sauna and Hot Tub
Killington
9.6 out of 10, Exceptional, (25 reviews)
"Great stay! Very convenient to slopes!"
United States
Conor D.
Trailside Village 5: Wood Stove, Private Sauna and Hot Tub

20. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is CA $324
CA $671 total
includes taxes & fees
Nov 22 - Nov 23
The Suites at Killington Center
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodstock. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated vacation home rental in Woodstock is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind. Another good choice for your trip to Woodstock is Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!.

How many vacation rentals are there in Woodstock?

Expedia has 37 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, Saskadena Six Ski Area and Green Mountain National Forest 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.