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

Search Winchester Cottage Rentals from CA $419

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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 Winchester cottages

A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

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)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is CA $273
CA $526 total
includes taxes & fees
Nov 9 - Nov 10
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A house with a deck, surrounded by trees and a grassy slope.

2. 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
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A small, single-story building with a front door and a small window.

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)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
United States
David W.
The price is CA $294
CA $419 total
includes taxes & fees
Nov 7 - Nov 8
Cozy Tiny House on Main Street. Fully Renovated.
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.
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Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Quiet, clean, safe area. Good breakfast- fruit, yogurt, waffles plus all the usual cereal, toast etc."
Martha 1-night trip
Posted 16 hours ago
The Putney Inn

Find out more about Winchester

Winchester Cottages information

Number of reviews
31
Accommodation
53 Cottages
Lowest Price
CA $419
Highest Price
CA $526

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