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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winchester vacation homes

An outdoor patio with wicker furniture, a lantern, and a wooden deck.

1. Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
The price is ￥21,201
￥26,112 total
includes taxes & fees
Dec 7 - Dec 8
Cozy Country Bungalow
A spacious living area with a dining table, chairs, a sofa, a TV, and a potted plant.

2. Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
The price is ￥21,123
￥32,883 total
includes taxes & fees
Nov 30 - Dec 1
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
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 reviews in Winchester

A spacious living room with a fireplace, leather sofas, a coffee table, and a large rug.
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast
North Dundas

10/10 Excellent

Annette made the most wonderful breakfast and was so accommodating in every way. It was a real delight, staying at her bed and breakfast.
United States
Brian
Reviewed September 17, 2025
Terrace Green Bed & Breakfast