A snow-covered town with a river running through it, surrounded by mountains and trees.

Search Winchester Cottage Rentals from CA $457

  • 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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winchester cottages

House (2 Bedrooms) | Interior

1. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
TV, books

2. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is CA $369
CA $457 total
includes taxes & fees
Aug 6 - Aug 7
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
House (3 Bedrooms) | Interior

3. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is CA $246
CA $611 total
includes taxes & fees
Aug 11 - Aug 12
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Super fun environment. Wish we had more time to stay there. In the middle of nowhere yet still close to food places and other activities."
Kathleen 1-night trip
Posted 6 hours ago
Vikings Villages Resort

Find out more about Winchester

Winchester Cottages information

Number of reviews
10
Accommodation
52 Cottages
Lowest Price
CA $457
Highest Price
CA $611

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Booking a cottage in Winchester is as easy as deciding on your travel dates and picking your ideal place for outdoor recreation and relaxation. From luxurious retreats to affordable properties and cottages that have amenities like a kitchenette, Expedia has something for all tastes. As for awesome deals? We've got you covered!
How can I find cheap cottages in Winchester?
The easiest way to get cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow your search results by amenities, budget and star rating to grab unbeatable deals in just a few keystrokes.

Explore a world of travel with Expedia