Title: Winchester Vacation Rentals from CA $150: Short-Term Rentals for 2025 | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx6344696)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6344696.Travel-Guide-Hotels)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6344696.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6344696.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Winchester Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Nov 17 - Nov 18](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2025-11-17&endDate=2025-11-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2025-11-18&endDate=2025-11-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6344696&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Winchester ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Vacation-Rentals.d6344696.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Vacation-Rentals.d6344696.Travel-Guide-VacationRentals) ## Top Winchester Hotel Reviews ![SureStay Hotel by Best Western Kemptville](//images.trvl-media.com/lodging/30000000/29060000/29059900/29059815/bde29736_y.jpg) ### SureStay Hotel by Best Western Kemptville 10/10 Excellent "Front Desk clerk was polite, and willing to accommodate us for a “family funeral “. Room was clean and comfortable, just what we were looking for. " [](https://expedia.ca/Ottawa-Hotels-SureStay-Hotel-By-Best-Western-Kemptville.h29059815.Hotel-Information) ### Hard Rock Hotel & Casino Ottawa 10/10 Excellent "Clean room. Friendly staff " [](https://expedia.ca/Ottawa-Hotels-Hard-Rock-Hotel-Casino-Ottawa.h105812923.Hotel-Information) ![Cedar Drive Inn](//images.trvl-media.com/lodging/13000000/12630000/12627100/12627006/9ed959d1_y.jpg) ### Cedar Drive Inn 10/10 Excellent "clean room, staff stayed up to let me in after closing. Friendly and relaxing. " [](https://expedia.ca/North-Stormont-Hotels-Cedar-Drive-Inn.h12627006.Hotel-Information) ![Kemptville Suites](//images.trvl-media.com/lodging/11000000/10090000/10082300/10082221/0b8174d1_y.jpg) ### Kemptville Suites 10/10 Excellent "Our suite was great for us. It was comfortable and well appointed. The weather was wet and rainy so we really enjoyed the gas fireplace. One suggestion would be to put a lamp in the sitting area. For people with "old eyes" it was hard to read printed material on the couch." [](https://expedia.ca/Ottawa-Hotels-Kemptville-Suites.h10082221.Hotel-Information) ![Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.](//images.trvl-media.com/lodging/120000000/119360000/119355200/119355194/fd00a486_y.jpg) ### Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport. 10/10 Excellent "House was clean, beds were comfortable and having black out curtains when traveling with littles ones was amazing. Would recommend! " [](https://expedia.ca/Ottawa-Hotels-Modern-Comfort-Private-View-30-Mins-To-Ottawa-Downtown-And-Airport.h119355194.Hotel-Information) ![McIntosh Country Inn & Conference Centre in Canada](//images.trvl-media.com/lodging/11000000/10050000/10044900/10044876/34f7482a_y.jpg) ### McIntosh Country Inn & Conference Centre in Canada 10/10 Excellent "just overall great" [](https://expedia.ca/South-Dundas-Hotels-McIntosh-Country-Inn-Conference-Centre-In-Canada.h10044876.Hotel-Information) ### Room in Ottawa close to the airport 10/10 Excellent "Amazing stay! The place was spotless, cozy, and in a great location. The host was very helpful, easy going and responsive, making everything easy from check-in to checkout. I would absolutely book again, thank you for a great experience." [](https://expedia.ca/Ottawa-Hotels-Room-In-Ottawa-Close-To-The-Airport.h120862808.Hotel-Information) ![Bed & Stay](//images.trvl-media.com/lodging/97000000/96800000/96798800/96798748/8bea93e1_y.jpg) ### Bed & Stay 10/10 Excellent "The place looks very new and it’s clean, the Moazzam was super good and he is reachable 24/7. The place is surrounded by great nature and it is very quiet and cool place to relax and enjoy your stay. " [](https://expedia.ca/Russell-Hotels-Bed-Stay.h96798748.Hotel-Information) ### Rideau River Retreat - Waterfront Home 10/10 Excellent "Quiet & Private: Ideal location for exploring Ottawa ON (try Union Street Kitchen's croissants before a guided tour of Rideau Hall). Also, just a short drive & quick border-crossing to the Frederick Remington Museum (western art & sculpture) in Ogdensburg NY. Local recommendations include the lamb rosemary meat pies made at B&H Grocery and the Tip-to-Tip trail, an easy 3-mile canal hike in Burritt’s Rapids. Many thanks to our exemplary hosts who quickly resolved any minor issues." [](https://expedia.ca/North-Grenville-Hotels-Rideau-River-Retreat-Waterfront-Home.h92840637.Hotel-Information) ## Find out more about Winchester **Everything you need to know about** **Winchester** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Winchester vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $150 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Winchester rentals** At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Winchester ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in Winchester](https://expedia.ca/Winchester-Private-Vacation-Homes.d6344696-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Winchester](https://expedia.ca/Winchester-Apartments.d6344696-aaApartments.Travel-Guide-Accommodation) - [Cottages in Winchester](https://expedia.ca/Winchester-Cottages.d6344696-aaCottages.Travel-Guide-Accommodation) - [B&B in Winchester](https://expedia.ca/Winchester-Bed-And-Breakfast.d6344696-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Winchester](https://expedia.ca/Winchester-Motels.d6344696-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in Winchester](https://expedia.ca/Winchester-Guest-Houses.d6344696-aaGuestHouses.Travel-Guide-Accommodation) - [Houseboats in Winchester](https://expedia.ca/Winchester-Houseboats.d6344696-aaHouseboats.Travel-Guide-Accommodation) - [Inns in Winchester](https://expedia.ca/Winchester-Inns.d6344696-aaInns.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a vacation rental in Winchester? > Yes, we offer vacation rentals near popular points of interest in Winchester, or you can go with a more remote option if you're looking for relaxation. ### What are some of the best vacation rentals in Winchester? > [RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa](https://www.expedia.ca/North-Dundas-Hotels-RARE-Tiny-House-2-BEDS-Free-WiFi-30m-To-Ottawa.h109911968.Hotel-Information): Visitors give good reviews to this Winchester vacation home rental, which is equipped with a fireplace, air-conditioning, and free 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 exploring the area, visit family-friendly sights like Calypso Water Park, or get outside and enjoy nature at Rideau River Provincial Park. In the larger area, you’ll find Domaine du Cervin and Place D'Embrun. ### What are vacation rentals like in Winchester? > Vacation rentals are privately owned accommodations you can book for a short or long stay in Winchester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you a great travel experience. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)