Search Cottages in Woodstock

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 54 Cottages in Woodstock with updated reviews, rates, and availability.

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great location close to Killington. Accurate listing. Nothing fancy but all the necessities available. Was clean and comfortable. Driveway was plowed early for easy access in/out."
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Living area

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Cozy Historic Hilltop Cottage with Mount Ascutney View
Cottage on the hill

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"This was the perfect cottage for a winter getaway. I was solo, but the home could have easily accommodated many more. I loved the vintage touches and had a nice time listening to the classic vinyl records while enjoying a glass of wine and watching it snow. I had dinner outside on the patio one night and the view was lovely. It is just a few minutes drive from Woodstock and Quechee and I visited both several times. The cottage was clean and had everything I needed. Highly recommend for a quiet,...
Cozy Historic Hilltop Cottage with Mount Ascutney View
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Living area

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Exterior

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (9)
"If you’re looking to spend a weekend with some friends at Killington this is definitely the most bang for your buck outside of the resort. 20 minute drive and plenty of plowed parking. "
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Weston Vacation Rental - Close to Ski Resorts!
Living area

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
Inviting Vermont Home On Mount Ascutney!
Living area

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
Idyllic Wallingford Retreat - Near Skiing & Hiking
Dining

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was the perfect place for 2 people to stay for a trip to Okemo. Everything we could have needed was available on the property, it was very clean and comfortable, and the hostess was great at communicating details ahead of time. Thanks for allowing us to use your property - I would love to return!"
Idyllic Wallingford Retreat - Near Skiing & Hiking
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Private kitchen

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Pet-friendly Claremont Vacation Rental!
Living area

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!
Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres
Wooded Waterfront Grantham Home < 10 Mi to Ski!
Terrace/patio

Wooded Waterfront Grantham Home < 10 Mi to Ski!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great atmosphere!"
Wooded Waterfront Grantham Home < 10 Mi to Ski!
Luxury Vermont Vacation Rental: Private Hot Tub!
Dining

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
3-acre Thetford Rental w/ River Access & Upgrades!
Private kitchen

3-acre Thetford Rental w/ River Access & Upgrades!

3.0 star property
3-acre Thetford Rental w/ River Access & Upgrades!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Outdoor dining

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Killington Area Escape w/ Deck, Views & Hot Tub!
Terrace/patio

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Lakefront Paradise Near Okemo & Killington
Property grounds

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Property grounds

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
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.
Don't see what you're looking for?
See all available properties in Woodstock
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

9.2 out of 10, Wonderful, (11)
"Everything was perfect "
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.

Frequently asked questions

Why book your cottage in Woodstock with Expedia?
We think that vacations should be stress-free, so if you’re on the lookout for cottages in Woodstock at an affordable rate, Expedia has your back. Save cash and choose an inexpensive option far away from the hustle and bustle, or book a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Woodstock?
Expedia can help you easily source cheap cottages in Woodstock. To reserve your dream stay in a few quick clicks, simply use the filter tool to tailor your search results by amenities, star rating and budget.