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
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 65 Cottages in Woodstock with updated reviews, rates, and availability.

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

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
Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
1 bedroom, free WiFi, bed sheets

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice time, great location"
The price is AED 574
AED 1,843 total
includes taxes & fees
7 Apr - 8 Apr
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (90)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House
Cozy Historic Hilltop Cottage with Mount Ascutney View
Exterior

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
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
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Interior

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!
Idyllic Wallingford Retreat - Near Skiing & Hiking
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, cookware/dishes/utensils

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
Pet-friendly Claremont Vacation Rental!
Terrace/patio

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Fridge, microwave, oven, stovetop

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

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

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Weston Vacation Rental - Close to Ski Resorts!
House (3 Bedrooms) | Interior

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
House (6 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Spruce Moose Cottage | Tiny House on 65 private acres
Fridge, oven, stovetop, cookware/dishes/utensils

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres
3-acre Thetford Rental w/ River Access & Upgrades!
Interior

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

3.0 star property
3-acre Thetford Rental w/ River Access & Upgrades!
Luxury Vermont Vacation Rental: Private Hot Tub!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
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!
Lakefront Paradise Near Okemo & Killington
Interior

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Wooded Waterfront Grantham Home < 10 Mi to Ski!
TV, fireplace

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!
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

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Outdoor dining

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (52)
"Perfect! The home was clean and comfortable for our group of four. Plenty of outdoor activities nearby. Woodstock has lovely shops and restaurants. We will be back."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Exterior

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (20)
"For peak leaf-peeping season, this place was a great deal for our group of 8 adults! We needed 5 of the 6 bedrooms. I used the 6th as my personal bathroom & dressing room. The house is well stocked with tea, coffee & Smores kits. The beds are really comfortable! The property is beautiful! We walked to the pizza place adjacent to the place. Meeting the owner, Andy, was so fun! It might be helpful for you to know: All of the bedrooms are upstairs, and the stairs are pretty steep. The bathrooms...
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
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?
Expedia has some superb cottages in Woodstock, so start planning for an unforgettable vacay on nature’s doorstep. If you have a fixed budget, choose how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect digs whatever your escape looks like.
How can I find cheap cottages in Woodstock?
The best way to compare cheap cottages in Woodstock is with Expedia’s user-friendly filter tool. Narrow down your search by budget, amenities and star rating to land unbeatable prices in just a few clicks.