Woodstock Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Browse Select Woodstock Vacation Homes

A charming 1820's farmhouse

10.0 out of 10, Exceptional, (27)
"this property had a very different feel because it was once an inn, which made it feel like we had the whole inn to ourselves, which was lovely. The place is spotless, everything you could possibly need is there, and it is beautifully decorated."
A charming 1820's farmhouse

Off Grid Glamping Shed with River Access

2.0 star property
Off Grid Glamping Shed with River Access

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Charming Cavendish Guesthouse

9.8 out of 10, Exceptional, (7)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
Charming Cavendish Guesthouse

The Carol - 10 minutes to Okemo & Newly Renovated

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The Carol - 10 minutes to Okemo & Newly Renovated

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (38)
"Awsome place to stay for a week! "
Spacious country home, beautiful sunsets, 40 acres

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
Okemo's Back Room - in the heart of the village on the shuttle route!

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great home, a stones throw from one of the best kept secrets in Vermont…Dan and Holly were very responsive, have a beautiful home that’s bigger than what I thought based on the listing.We love the ski mountain right there - perfect for intermediate and beginner skiers. My kids loved it!!"
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

10.0 out of 10, Exceptional, (1)
"Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again."
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Luxury Graduation and Reunion Rental- Walk to Dartmouth!

10.0 out of 10, Exceptional, (2)
"Amazing house within walking distance of the campus. Would definitely recommend to anyone."
Luxury Graduation and Reunion Rental- Walk to Dartmouth!

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

The Bridgewater House | Game Room | Hiking | Porch

9.6 out of 10, Exceptional, (7)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The Bridgewater House | Game Room | Hiking | Porch

Acres & Views! Firepit, BBQ | Bayley Way Getaway

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The Snowshed Steps at Mt Green: Walk-to-Lifts Killington Condo w/ Pools, AC, Fireplace & Shuttle!

The Snowshed Steps at Mt Green: Walk-to-Lifts Killington Condo w/ Pools, AC, Fireplace & Shuttle!

Ski home Mountain Views near Killington/Woodstock

10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Ski home Mountain Views near Killington/Woodstock
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Woodstock Hotel Reviews

Find out more about Woodstock

Find out more about Woodstock

Woodstock Vacation Homes information

Number of reviews
339
Accommodation
942 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia