Photo by George Sykes

Search Cottages in South 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 51 Cottages in South Woodstock with updated reviews, rates, and availability.

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

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.

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 price is AED 566
AED 1,842 total
includes taxes & fees
5 Mar - 6 Mar
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!

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

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!

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

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!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!

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!

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

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!

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!

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

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Near Okemo Slopes: Peaceful Home w/ Trail Access

3.0 star property
Near Okemo Slopes: Peaceful Home w/ Trail Access

Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

3.0 star property
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

Ski, Hike & Fish: Modern Rutland Home

3.0 star property
Ski, Hike & Fish: Modern Rutland Home
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 South Woodstock
Save an average of 15% on thousands of hotels when you're signed in

Other property types in South Woodstock

Mountain Green

2.0 star property
6.4 out of 10, (7)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is AED 686
AED 920 total
includes taxes & fees
10 Mar - 11 Mar
Mountain Green

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.2 out of 10, Wonderful, (67)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is AED 1,179
AED 2,196 total
includes taxes & fees
9 Mar - 10 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.4 out of 10, Very Good, (16)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is AED 485
AED 1,385 total
includes taxes & fees
11 Mar - 12 Mar
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes
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 South Woodstock with Expedia?
Expedia has some great cottages in South Woodstock, so start packing for an unforgettable vacation on nature’s doorstep. If you have a set budget, choose how much you want to spend and the star rating of your property. Or, make your way to the filters to search for cottages with free WiFi or a kitchen. We’ll help you find the right digs whatever your style of travel or plans.
How can I find cheap cottages in South Woodstock?
Expedia is here to help you look for cheap cottages in South Woodstock. To lock in a superb stay in a few clicks, try out our convenient filter tool to tailor your search results by budget, amenities and star rating.