Title: Winchester Vacation Home Rentals from CA $358: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d183815.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d183815.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d183815.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d183815.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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Interior](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/fbcb2c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/6a74bc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/46e0bd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/0eef6fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique stay, hot tub, secluded Peebles 9.2/10 Wonderful (15) "This is an amazing property and we will be returning because it was so luxurious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $170 CA $358 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Peebles-Hotels-Unique-Stay.h107475752.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/009ac7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/w1178h1365x6y2-34534523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/8fa1af1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/21cfff4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA! Dover 9.6/10 Exceptional (7) "This was a great stay. Very easy to find and in a good area. Very clean and nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda R. CA $283 CA $389 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Dover-Hotels-Experience-Peace.h111652604.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/b7180dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/f7a1cb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/ab991283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/1be36898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR! Hillsboro 9.6/10 Exceptional (31) "Super clean, comfortable and convenient to visit the Arc of Appalachia preserves nearby. There are several beautiful ones including the Highland Nature Sanctuary. The pups loved it too. The kitchen was well-stocked, beds comfortable and nice sun-room and back-yard." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ST8851 CA $251 CA $559 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hillsboro-Hotels-LAKE-HOUSE-ON-ROCKY-FORK.h71964019.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/cc7c5bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/33289191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/aeb0e2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/0e218996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage Hillsboro 10/10 Exceptional (1) "Words can’t describe it and pictures don’t do justice. It’s such a cool place. Everyone in our group of 8 ladies absolutely loved this property. We had two pool days, relaxed in the hot tub, enjoyed the fire pit, watched movies in the theater room and loved every minute of how incredibly peaceful the location is. The hosts have thought of everything and welcomed us with some extras to help make the stay even more perfect. We had such a wonderful time at Country Cornerstone Retreat. We are... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robyn T. CA $529 CA $1,043 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hillsboro-Hotels-Country-Cornerstone-Retreat.h115554816.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-08&endDate=2025-11-09®ionId=183815&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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-Private-Vacation-Homes.d183815-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Private-Vacation-Homes.d183815-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Brown's Motel Aberdeen](//images.trvl-media.com/lodging/11000000/10260000/10253500/10253418/4ca9fc0f_y.jpg) ### Brown's Motel Aberdeen 10/10 Excellent "Perfect for an overnight stay visiting historical sites " [](https://expedia.ca/Hillsboro-Hotels-Browns-Motel-Aberdeen.h10253418.Hotel-Information) ![Glamping Cabin | Huge Window | Tree House Feel](//images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/4e85dea7_y.jpg) ### Glamping Cabin | Huge Window | Tree House Feel 4/10 Poor " The shared "kitchen" cabin is a roofed area open on 3 sides . There is a very old dirty microwave on top of a wooden stool and a very used, unclean refrigerator in the open air, there are NO cooking surfaces, No sink to wash dishes, No heated area area to eat or cook food . Do not come expecting to prepare food at this place unless you bring your own equipment. The kitchen area is filthy and disorganized , like cooking in someones garage. A dog in one of the fenced units was outside barking all night for multiple nights and the long trip to the shared bathroom has led to the area around each cabin being used for open air urination , you can smell it as you walk by. " [](https://expedia.ca/Glamping-Cabin-Huge-Window-Tree-House-Feel.h76018506.Hotel-Information) ![Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!](//images.trvl-media.com/lodging/34000000/33950000/33949400/33949345/ce32c6b5_y.jpg) ### Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee! 10/10 Excellent "The host checked in with us shortly after we checked in to make sure we didn't need anything, and was sure to let us know we could ask for anything we needed during our stay. The cabin was beautiful, and it was a relaxing stay in a peaceful, quiet location. The cabin was very clean and cozy, and they had plenty of supplies for the entire trip. Would definitely like to stay again! " [](https://expedia.ca/Blue-Creek-Hotels-Get-Away-From-It-All-Restored-1800-Log-Cabin-Modern-Amenities-40-Private-Acres.h33949345.Hotel-Information) ![Country Nights Inn](//images.trvl-media.com/lodging/107000000/106620000/106617100/106617030/e186aa05_y.jpg) ### Country Nights Inn 10/10 Excellent "This place was great for an overnight stay. Clean and comfortable. The owners were very proactive in communication and made sure we had what we needed. The internet was just a touch slow but could easily run a Zoom meeting or video calls. " [](https://expedia.ca/West-Union-Hotels-Country-Nights-Inn.h106617030.Hotel-Information) ![Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !](//images.trvl-media.com/lodging/30000000/29920000/29913200/29913121/43ca7232_y.jpg) ### Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake ! 10/10 Excellent "Very clean, well equipped property. Nice, quiet area. Property owner could not have been nicer!" [](https://expedia.ca/Hillsboro-Hotels-Newly-Built-Rustic-3-Bedroom-Cabin-With-A-One-Acre-Fishing-Lake.h29913121.Hotel-Information) ![Cozy private getaway built for couples to reconnect !! ](//images.trvl-media.com/lodging/100000000/99850000/99846400/99846345/c709cc75_y.jpg) ### Cozy private getaway built for couples to reconnect !! 10/10 Excellent "The cabin was exactly as described and pictured. Very clean, great getaway! The hottub (which was a big draw) was easy to use and clean. Access to good hiking and nature. " [](https://expedia.ca/West-Union-Hotels-Cozy-Private-Getaway-Built-For-Couples-To-Reconnect.h99846345.Hotel-Information) ![Beverly hills inn](//images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418_y.jpg) ### Beverly hills inn 10/10 Excellent "The staff is amazing " [](https://expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information) ![Peaceful cabin with spectacular river and scenic views.](//images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/fbed2d1d_y.jpg) ### Peaceful cabin with spectacular river and scenic views. 10/10 Excellent "Great location. " [](https://expedia.ca/Aberdeen-Hotels-Peaceful-Cabin-With-Spectacular-River-And-Scenic-Views-Along-With-Great-Sunsets.h105562236.Hotel-Information) ![French Quarter Inn](//images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/w1000h451x0y0-8ba0d251_y.jpg) ### French Quarter Inn 10/10 Excellent "The hotel was great as we were in the town to do family research and it was quiet and great for what we were doing." [](https://expedia.ca/Maysville-Hotels-French-Quarter-Inn.h15589406.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 53 | | --- | --- | | Accommodation | 49 Vacation Homes | | Lowest Price | CA $358 | | Highest Price | CA $1,043 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Peebles](https://www.expedia.ca/5Star-Peebles-Hotels.s50-0-d6195740.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sardinia](https://www.expedia.ca/5Star-Sardinia-Hotels.s50-0-d553248634983507551.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d6344064-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Hotel-With-Pool.0-0-d6344064-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Hotels-With-Balconies.0-0-d6344064-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - 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