Winchester Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchester holiday rentals

Interior
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)

M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)

M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
St-Albert
10.0 out of 10, Exceptional, (6)
"We enjoyed our stay here. Propert was clean and quiet. Found no priblems when staying here. Would highly recommend. "
Canada
Yolanda
The price is HK$767
HK$1,047 total
includes taxes & fees
2 Jan - 3 Jan 2026
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Fridge, microwave, oven, stovetop
Cozy Country Bungalow

Cozy Country Bungalow

Cozy Country Bungalow
Mountain
The price is HK$1,074
HK$1,393 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Country Bungalow
Private kitchen
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr

Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr

Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Russell
2.0 out of 10, (1)
"This property was listed as 3 Bedrooms / 1 Bath BUT, after reserving, I was told it was a Single Room with a SHARED Bath!! The listing explicitly says, per the VRBO guidelines, that you have the whole house and only share with your family. I cancelled immediately BUT have not heard from either the Property Owner or VRBO about a REFUND. NOT ACCEPTAB:E"
Canada
Mike
The price is HK$481
HK$850 total
includes taxes & fees
28 Dec - 29 Dec
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
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

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

10/10 Excellent
"The casino and hotel were very well kept. Rooms were modern and clean and the staff were great! Very helpful. I’m already planning my next visit. "
Emily Sonya 1-night trip
Posted 4 days ago
Hard Rock Hotel & Casino Ottawa

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa: This highly rated holiday home rental in Winchester is equipped with a fireplace, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Winchester?

While you're exploring the area, Rideau River Provincial Park and Ferguson Forest Dog Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Place D'Embrun and Osgoode Village Community Centre.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.