Winchester Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Winchester holiday rentals

Seasonal outdoor pool

Doran Bay Resort

Doran Bay Resort
2.5 star property
South Dundas
7.8 out of 10, Good, (21 reviews)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
Canada
Peg
The price is HK$725
HK$1,111 total
includes taxes & fees
23 May - 24 May
Doran Bay Resort
Fridge, microwave, oven, stovetop

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 reviews)
"As described, absolutely clean and comfortable"
Canada
linda r.
The price is HK$773
HK$1,048 total
includes taxes & fees
9 Jun - 10 Jun
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Smart TV, computer monitors, printers

A beautiful 2bedroom in-law suite with separate entrance and complete privacy.

A beautiful 2bedroom in-law suite with separate entrance and complete privacy.
Limoges
9.0 out of 10, Wonderful, (2 reviews)
"Easy to find , quiet neighborhood, communication was excellent, good value"
Canada
Joe
The price is HK$807
HK$1,559 total
includes taxes & fees
19 May - 20 May
A beautiful 2bedroom in-law suite with separate entrance and complete privacy.
TV, fireplace

The Meadow House, Country Retreat

The Meadow House, Country Retreat
Russell
The price is HK$716
HK$983 total
includes taxes & fees
1 Jun - 2 Jun
The Meadow House, Country Retreat
Smart TV

Entire Suite in Kemptville, Ontario, Canada

Entire Suite in Kemptville, Ontario, Canada
Kemptville
7.8 out of 10, Good, (7 reviews)
"Wonderful 2 nights stay. Clean, friendly, safe and very spacious. "
Canada
Natasha
The price is HK$744
HK$1,481 total
includes taxes & fees
31 May - 1 Jun
Entire Suite in Kemptville, Ontario, Canada
Outdoor dining

Cozy Country Bungalow

Cozy Country Bungalow
Mountain
10.0 out of 10, Exceptional, (1 review)
"Nice"
Canada
Marko I.
The price is HK$1,082
HK$1,397 total
includes taxes & fees
25 May - 26 May
Cozy Country Bungalow
Interior

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 review)
"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$487
HK$854 total
includes taxes & fees
14 May - 15 May
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

McIntosh Country Inn & Conference Centre in Canada

McIntosh Country Inn & Conference Centre in Canada

8/10 Good
"Bring your own pillow bc these ones are quite lumpy Everything else was great"
Tasha 1-night trip
Posted 1 hour ago
McIntosh Country Inn & Conference Centre in Canada

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
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  • 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 WiFi 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 Russell Township Dog Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Osgoode Village Community Centre and Baxter Conservation Area.

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.