Winchester Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Winchester

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 HK$799
HK$1,399 total
includes taxes & fees
2 Sept - 3 Sept
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Doran Bay Resort
Seasonal outdoor pool

Doran Bay Resort

2.5 star property
7.8 out of 10, Good, (21)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
The price is HK$701
HK$1,079 total
includes taxes & fees
3 Sept - 4 Sept
Doran Bay Resort
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Private kitchen

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

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"
The price is HK$479
HK$847 total
includes taxes & fees
2 Sept - 3 Sept
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Interior

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

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay here. Propert was clean and quiet. Found no priblems when staying here. Would highly recommend. "
The price is HK$761
HK$1,038 total
includes taxes & fees
3 Sept - 4 Sept
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Beautiful Home with castor river view
Fridge, microwave, oven, stovetop

Beautiful Home with castor river view

7.0 out of 10, Good, (17)
"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 HK$763
HK$1,296 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful Home with castor river view
Entire Suite in Kemptville, Ontario, Canada
Smart TV

Entire Suite in Kemptville, Ontario, Canada

6.0 out of 10, (3)
"Everything was fine for our overnight stay. Was not expecting an apartment but other than that the stay was comfortable."
The price is HK$659
HK$1,369 total
includes taxes & fees
1 Sept - 2 Sept
Entire Suite in Kemptville, Ontario, Canada
Hot Tub | Dock | Swimming | Close To Ottawa
Property grounds

Hot Tub | Dock | Swimming | Close To Ottawa

10.0 out of 10, Exceptional, (5)
"Nice and secluded. The dock has incredible views. Sandy bottom, clear water, we really enjoyed our stay."
Hot Tub | Dock | Swimming | Close To Ottawa
Unique houseboat rental with private dock and land on the historic Rideau River.
Dining

Unique houseboat rental with private dock and land on the historic Rideau River.

9.6 out of 10, Exceptional, (10)
"This property is in a lovely location with some marvellous outdoor options. It is close enough to Ottawa to be able to experience all the area has to offer yet far enough out to find peaceful relaxation if you prefer. The houseboat is such a unique experience. The host is very helpful and personable. "
Unique houseboat rental with private dock and land on the historic Rideau River.
Rideau River Retreat - Waterfront Home
Property grounds

Rideau River Retreat - Waterfront Home

10.0 out of 10, Exceptional, (13)
"Loved my stay! It’s a beautiful property and the host is great! Definitely would recommend!"
Rideau River Retreat - Waterfront Home
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The price is HK$813
HK$1,774 total
includes taxes & fees
4 Sept - 5 Sept
The “Old School” • Historic Town • Free Parking
Waterfront Retreat - South Nation River
Fridge, microwave, oven, stovetop

Waterfront Retreat - South Nation River

10.0 out of 10, Exceptional, (21)
"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 HK$1,065
HK$1,382 total
includes taxes & fees
2 Sept - 3 Sept
Cozy Country Bungalow
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
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
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.
Newly Renovated Private 2 bed with 1 bath Getaway
Fridge, microwave, oven, stovetop

Newly Renovated Private 2 bed with 1 bath Getaway

8.8 out of 10, Excellent, (5)
"Exactly where you’d want to stay, close to everything, secure location. Excellent communication, thank you again!"
Newly Renovated Private 2 bed with 1 bath Getaway
A beautiful 2bedroom in-law suite with separate entrance and complete privacy.
Smart TV, computer monitors, printers

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

8.0 out of 10, Very good, (1)
"Easy to find , quiet neighborhood, communication was excellent, good value"
A beautiful 2bedroom in-law suite with separate entrance and complete privacy.
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The price is HK$811
HK$1,776 total
includes taxes & fees
4 Sept - 5 Sept
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
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

Find out more about Winchester

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:

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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 exploring the area, visit family-friendly sights like Calypso Water Park, or get outside and enjoy nature at Russell Township Dog Park. 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.