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

Compare 56 Cottages in South Woodstock with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (7)
"Obsessed with this house! It was perfect for 2 couples and our pups for a relaxing fall weekend. Rooms were cozy, updated and super clean. The hot tub, fire pit by the river and big kitchen were highlights. I really appreciated the hospitality of having amenities like spices, coffee filters, shampoo & conditioner, laundry detergent, etc. Would book again!"
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

Charming Cavendish Cottage: All-Season Retreat!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Such a wonderful and warm home. Other than condiments the kitchen was well stocked with dishes, cups and small appliances. The back screened in porch was a peaceful retreat for morning coffee and devotions and a great place to wind down at night. The owner was very nice and accommodating. The minute we walked in we were in awe of Rosehill Cottage. We will definitely stay here again if we are in the area."
Charming Cavendish Cottage: All-Season Retreat!

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

9.2 out of 10, Wonderful, (15)
"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

9.6 out of 10, Exceptional, (9)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (75)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

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!

Weston Vacation Rental - Close to Ski Resorts!

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

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!

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

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

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

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!

Charming Cavendish Cottage: All-season Retreat!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent property and host. House was comfortable and inviting with all the amenities one could ask for. Beautiful grounds and a pond on property. We will definitely go back. "
Charming Cavendish Cottage: All-season Retreat!

The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very comfortable. Check-in was simple, plenty of communication and prompt replies. Would absolutely stay at this property again. "
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

Vermont Retreat - 8 Mi to Killington Ski Area

3.0 star property
Vermont Retreat - 8 Mi to Killington Ski Area

Duplex Unit, 2 Mi to Chittenden Reservoir!

3.0 star property
Duplex Unit, 2 Mi to Chittenden Reservoir!

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
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

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

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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?
Reserving a cottage in South Woodstock is as easy as clicking on your travel dates and picking your ideal place for a vacation in nature. From high-end retreats to budget-friendly stays and cottages that include amenities like laundry facilities, Expedia has something for all tastes and styles. As for terrific deals? We’ve got you covered!
How can I find cheap cottages in South Woodstock?
With Expedia’s filter tool, booking cheap cottages in South Woodstock is a cinch. To discover accommodations that’ll make your hip pocket happy, refine your search by amenities, star rating and budget.