Search Vacation Homes in Winchester from CA $135

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Winchester Vacation Homes

Beautiful Home with castor river view
Fridge, microwave, oven, stovetop

Beautiful Home with castor river view

7.2 out of 10, Good, (16)
"Was attending an event in the area; this property was well situated for our needs with shops and amenities nearby. Property was clean and well kept. "
The price is CA $135
CA $229 total
includes taxes & fees
Aug 26 - Aug 27
Beautiful Home with castor river view
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Fridge, microwave, oven, stovetop

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

10.0 out of 10, Exceptional, (5)
"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"
The price is CA $142
CA $248 total
includes taxes & fees
Aug 26 - Aug 27
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Waterfront Retreat - South Nation River
Fridge, microwave, oven, stovetop

Waterfront Retreat - South Nation River

10.0 out of 10, Exceptional, (20)
"Beautiful accommodation, very modernized, the house was very climate controlled for our comfort, it was awesome to wake up and enjoy a coffee on the back deck overlooking the water. Everything a family needs to have foe a comfortable stay. Thanks so much Chris"
Waterfront Retreat - South Nation River
Cozy Country Bungalow
Fridge, microwave, oven, stovetop

Cozy Country Bungalow

The price is CA $189
CA $245 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Country Bungalow
Quiet Riverfront , Pet friendly
Dining

Quiet Riverfront , Pet friendly

10.0 out of 10, Exceptional, (4)
"The place was perfect for 6 people. We spent 1 night and the rooms were spacious. The neighbourhood was really calm."
Quiet Riverfront , Pet friendly
Rideau River Getaway
Interior

Rideau River Getaway

10.0 out of 10, Exceptional, (2)
"Lots to do in the area and great place"
Rideau River Getaway
Inviting 1 Bedroom Fully Furnished smoke-free Guest House
Fridge, microwave, oven, stovetop

Inviting 1 Bedroom Fully Furnished smoke-free Guest House

10.0 out of 10, Exceptional, (4)
"A great place to stay to visit Ottawa and surrounding area. Very close to Parc Calypso (the waterpark), 30 minutes to Ottawa. Very bucolic and peaceful surroundings."
Inviting 1 Bedroom Fully Furnished smoke-free Guest House
Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.
Fridge, microwave, oven, stovetop

Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.

Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The price is CA $177
CA $358 total
includes taxes & fees
Aug 25 - Aug 26
The “Old School” • Historic Town • Free Parking
Elegance and serenity on Parkview Terr/Élégance et calme sur Parkview Terr
Interior

Elegance and serenity on Parkview Terr/Élégance et calme sur Parkview Terr

Elegance and serenity on Parkview Terr/Élégance et calme sur Parkview Terr
Furnished Two Bedroom Waterfront
Terrace/patio

Furnished Two Bedroom Waterfront

Furnished Two Bedroom Waterfront
Manotick waterfront property. Walking distance to pubs restaurants. groceries.
Private kitchen

Manotick waterfront property. Walking distance to pubs restaurants. groceries.

Manotick waterfront property. Walking distance to pubs restaurants. groceries.
Luxurious 2 bedroom house.Close to amenities, airport,downtown and EY centre.
View from property

Luxurious 2 bedroom house.Close to amenities, airport,downtown and EY centre.

Luxurious 2 bedroom house.Close to amenities, airport,downtown and EY centre.
Family home near Calypso park
Dining

Family home near Calypso park

Family home near Calypso park
Lake House 8 Min from Airport sleeps 13
Property grounds

Lake House 8 Min from Airport sleeps 13

Lake House 8 Min from Airport sleeps 13
Century old charming little home to unwind
Exterior

Century old charming little home to unwind

Century old charming little home to unwind
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.
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

SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

10/10 Excellent
"Great, friendly, professional service! Clean and spacious rooms. Wonderful stay."
Kathryn 1-night trip
Posted 6 hours ago
SureStay Hotel by Best Western Kemptville