Title: Winchester Vacation Rentals from CA $149: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+North+Dundas%2C+Ontario%2C+Canada&regionId=6344696&latLong=45.092877%2C-75.35299&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+North+Dundas%2C+Ontario%2C+Canada&regionId=6344696&latLong=45.092877%2C-75.35299&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+North+Dundas%2C+Ontario%2C+Canada&regionId=6344696&latLong=45.092877%2C-75.35299&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+North+Dundas%2C+Ontario%2C+Canada&regionId=6344696&latLong=45.092877%2C-75.35299&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

![Hard Rock Hotel & Casino Ottawa](https://images.trvl-media.com/lodging/106000000/105820000/105813000/105812923/e6ad2691_y.jpg)

### Hard Rock Hotel & Casino Ottawa

10/10 Excellent

"Clean and great centre"

[](https://expedia.ca/Ottawa-Hotels-Hard-Rock-Hotel-Casino-Ottawa.h105812923.Hotel-Information)

![Kemptville Suites](https://images.trvl-media.com/lodging/11000000/10090000/10082300/10082221/0b8174d1_y.jpg)

### Kemptville Suites

10/10 Excellent

"Beautiful place"

[](https://expedia.ca/Ottawa-Hotels-Kemptville-Suites.h10082221.Hotel-Information)

![Stunning Home close to Ottawa](https://images.trvl-media.com/lodging/121000000/120070000/120068200/120068174/w1179h736x0y0-2a7cba21_y.jpg)

### Stunning Home close to Ottawa

10/10 Excellent

"Great location, very clean and bright. Host was very accommodating. Will definitely be back!"

[](https://expedia.ca/Ottawa-Hotels-Stunning-Home-Close-To-Ottawa.h120068174.Hotel-Information)

![McIntosh Country Inn & Conference Centre in Canada](https://images.trvl-media.com/lodging/11000000/10050000/10044900/10044876/34f7482a_y.jpg)

### McIntosh Country Inn & Conference Centre in Canada

10/10 Excellent

"Spotless"

[](https://expedia.ca/South-Dundas-Hotels-McIntosh-Country-Inn-Conference-Centre-In-Canada.h10044876.Hotel-Information)

![Terrace Green Bed & Breakfast](https://images.trvl-media.com/lodging/11000000/10590000/10584000/10583909/db97a21e_y.jpg)

### Terrace Green Bed & Breakfast

10/10 Excellent

"Everything was great had a great time highly recommend "

[](https://expedia.ca/North-Dundas-Hotels-Terrace-Green-Bed-Breakfast.h10583909.Hotel-Information)

![SureStay Hotel by Best Western Kemptville](https://images.trvl-media.com/lodging/30000000/29060000/29059900/29059815/bde29736_y.jpg)

### SureStay Hotel by Best Western Kemptville

10/10 Excellent

"Staff, cleanliness! Good stay! "

[](https://expedia.ca/Ottawa-Hotels-SureStay-Hotel-By-Best-Western-Kemptville.h29059815.Hotel-Information)

![Bed & Stay](https://images.trvl-media.com/lodging/97000000/96800000/96798800/96798748/8bea93e1_y.jpg)

### Bed & Stay

10/10 Excellent

"Clean house and great person to deal with. Very good and simple instructions for a smooth and nice stay."

[](https://expedia.ca/Russell-Hotels-Bed-Stay.h96798748.Hotel-Information)

![KC's Country Inn](https://images.trvl-media.com/lodging/9000000/8790000/8782500/8782416/efc2920f_y.jpg)

### KC's Country Inn

10/10 Excellent

"C’est très bien comme aider à trouver des hôtels et des hébergements à bas prix."

[](https://expedia.ca/Ottawa-Hotels-KCs-Country-Inn.h8782416.Hotel-Information)

![Rideau River Retreat - Waterfront Home](https://images.trvl-media.com/lodging/93000000/92850000/92840700/92840637/d4a024d4_y.jpg)

### Rideau River Retreat - Waterfront Home

10/10 Excellent

"We had such a wonderful experience. Our host Meghan was always quickly available and provided all the information we needed for a trouble free stay. The cottage is lovely and is the perfect place for both winter or summer getaways."

[](https://expedia.ca/North-Grenville-Hotels-Rideau-River-Retreat-Waterfront-Home.h92840637.Hotel-Information)

## Find out more about Winchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d6344696-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d6344696-aaApartments.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d6344696-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Winchester ](https://expedia.ca/Winchester-Houseboats.d6344696-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d6344696-aaMotels.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d6344696-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d6344696-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Winchester?

### What are some of the best vacation rentals in Winchester?

### What can I see and do in Winchester?

### What are vacation rentals like in Winchester?

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