A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Search Woodstock Cottage Rentals from CA $264

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Woodstock cottages

A white house with a red roof and a hammock in the yard.

1. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.4 out of 10, Exceptional, (20 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is CA $147
CA $264 total
includes taxes & fees
Nov 4 - Nov 5
Addie's Place: A Quiet and Quirky Guesthouse
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

2. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $224
CA $693 total
includes taxes & fees
Nov 4 - Nov 5
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
A cabin with a porch, a garage, and a dirt driveway surrounded by trees.

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

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (22 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
A green wooden house with a sloped roof and a front porch.

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is CA $1,920
CA $3,005 total
includes taxes & fees
Nov 6 - Nov 7
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodstock Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Cosy and lovely. Couldnt have been nicer. The breakfast muffins were homemade and the bestbive ever had"
chiara 1-night trip
Posted 1 hour ago
On The River Inn

Find out more about Woodstock

Woodstock Cottages information

Number of reviews
42
Accommodation
90 Cottages
Lowest Price
CA $264
Highest Price
CA $3,005

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.
What is there to do in Woodstock near my cottage?
You'll find loads of fabulous things that'll fill up your itinerary in Woodstock. Discover well-known attractions like Dana House Museum, Taftsville Covered Bridge and Marsh-Billings-Rockefeller National Historical Park. Woodstock Country Club, Billings Farm and Museum and Woodstock Town Hall Theatre are also visitor favorites.

Explore a world of travel with Expedia