Title: Winchester Vacation Rentals from CA $150: Short-Term Rentals for 2026 | Expedia.ca

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# Winchester Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-01-11&endDate=2026-01-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 12 - Jan 13](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-01-12&endDate=2026-01-13&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## 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=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=APARTMENT)

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=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=VACATION_HOME)

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=2026-04-11&d1=2026-04-11&endDate=2026-04-14&d2=2026-04-14&lodging=COTTAGE)

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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

"The room was perfect, staff is always friendly! Looking forward to our next stay!! "

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

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

### Kemptville Suites

10/10 Excellent

"very clean, felt like home, nice part of town, netflix, "

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

"Did not know we had a free breakfast. We paid for our breakfast. breakfast we very good. nice clean rooms we enjoyed out stay."

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

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

### Bed & Stay

10/10 Excellent

"Outstanding stay. Beautiful new construction property which was extremely clean and well presented. Good communication with the host. Master ensuite was excellent!!"

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

"Close to the town 4 minutes away"

[](https://expedia.ca/Ottawa-Hotels-SureStay-Hotel-By-Best-Western-Kemptville.h29059815.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 a great stay and loved the house and location "

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

![RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa](https://images.trvl-media.com/lodging/110000000/109920000/109912000/109911968/371d4ba6_y.jpg)

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

10/10 Excellent

"It was a great place to stay, we will be back!!! "

[](https://expedia.ca/North-Dundas-Hotels-RARE-Tiny-House-2-BEDS-Free-WiFi-30m-To-Ottawa.h109911968.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

"The bed was exceptionally comfortable, Annette warm and inviting, and the breakfast delicious. "

[](https://expedia.ca/North-Dundas-Hotels-Terrace-Green-Bed-Breakfast.h10583909.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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- [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d6344696-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

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### What are vacation rentals like in Winchester?

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