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

Search Winchester Cottage Rentals from CA $389

  • 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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester cottages

Exterior

1. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is CA $273
CA $551 total
includes taxes & fees
Sep 23 - Sep 24
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Exterior

2. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is CA $245
CA $389 total
includes taxes & fees
Sep 21 - Sep 22
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

3. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is CA $294
CA $443 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Tiny House on Main Street. Fully Renovated.
House (3 Bedrooms) | Interior

4. 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 $204
CA $563 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
TV, books

5. 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 $529
CA $642 total
includes taxes & fees
Sep 27 - Sep 28
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Though it's not a luxury hotel, the staff is exceptionally nice & helpful. the property is clean, there are carts for moving luggage, the breakfast service is fine. It's quiet. the bathroom is spacious w.nice towels & toiletries. Parking is easy."
Robert 1-night trip
Posted 8 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Winchester Cottages information

Number of reviews
53
Accommodation
52 Cottages
Lowest Price
CA $389
Highest Price
CA $642

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