Title: Winchester Vacation Home Rentals from CA $311: 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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/0eef6fff.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) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107480000/107475800/107475752/479d0a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique stay, hot tub, secluded [](https://www.expedia.ca/Peebles-Hotels-Unique-Stay.h107475752.Hotel-Information) Peebles 8.8/10 Excellent (18) "Property was clean and a unique property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $168 CA $353 total includes taxes & fees Dec 22 - Dec 23 [](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) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/ee2dc8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/8e88297d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/cfe8fda0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA! [](https://www.expedia.ca/Dover-Hotels-Experience-Peace.h111652604.Hotel-Information) Dover 9.6/10 Exceptional (8) "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 $223 CA $311 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Dover-Hotels-Experience-Peace.h111652604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123370000/123363500/123363495/08bcccb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123370000/123363500/123363495/87b5bf83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123370000/123363500/123363495/9da5eef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123370000/123363500/123363495/0fbf1032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2-bedroom house in Ripley with AC, Coffee Bar and Firepit. Pet friendly. [](https://www.expedia.ca/Ripley-Hotels-Cozy-2-Bedroom-House-In-Ripley-With-AC.h123363495.Hotel-Information) Ripley CA $153 CA $250 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ripley-Hotels-Cozy-2-Bedroom-House-In-Ripley-With-AC.h123363495.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/1be36898.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) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/72000000/71970000/71964100/71964019/009a270a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR! [](https://www.expedia.ca/Hillsboro-Hotels-LAKE-HOUSE-ON-ROCKY-FORK.h71964019.Hotel-Information) Hillsboro 9.6/10 Exceptional (31) "Very clean and neat, everything was as described, the grill was a bit rusty but overall was a wonderful experience!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troy B. CA $247 CA $543 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Hillsboro-Hotels-LAKE-HOUSE-ON-ROCKY-FORK.h71964019.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119490000/119487100/119487055/08c41652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/120000000/119490000/119487100/119487055/a00e585d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119490000/119487100/119487055/540636d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119490000/119487100/119487055/23b6c5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Cabin-Couple's only Hot Tub Getaway [](https://www.expedia.ca/Hillsboro-Hotels-A-Romantic-Retreat-Just-You-And-Your-Person.h119487055.Hotel-Information) Hillsboro 9.8/10 Exceptional (6) CA $240 CA $387 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Hillsboro-Hotels-A-Romantic-Retreat-Just-You-And-Your-Person.h119487055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112610000/112608800/112608755/w1170h777x0y5-0de50e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/113000000/112610000/112608800/112608755/4de714c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/113000000/112610000/112608800/112608755/43f40352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112610000/112608800/112608755/e430e7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More [](https://www.expedia.ca/Peebles-Hotels-Delightful-A-Frame-Home-On-20-Acres-With-Hiking-Trails.h112608755.Hotel-Information) Peebles 9.8/10 Exceptional (6) "Was clean well stocked and everything wee we’re looking for " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antony W. CA $273 CA $421 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Peebles-Hotels-Delightful-A-Frame-Home-On-20-Acres-With-Hiking-Trails.h112608755.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/25314d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/3e720f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/w1860h1386x0y0-e0fa747e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/468750cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Tiny Home Getaway! [](https://www.expedia.ca/Sardinia-Hotels-Perfect-Tiny-Home-Getaway.h101384896.Hotel-Information) Sardinia 6.0/10 (1) "I really never received any information really about checking in or out. Received email with code to door. Got there had no water at bathroom sink told host said probably clogged pipe never offered to come look. Messaged at 9 am about checking out n still haven’t heard back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan A. CA $123 CA $238 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Sardinia-Hotels-Perfect-Tiny-Home-Getaway.h101384896.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/0855e65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/8d227e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/108892a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/6d6b9611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cornerstone Retreat Upstairs - Hot Tub, Sauna, Grill, Fire Pit, Massage [](https://www.expedia.ca/Lynchburg-Hotels-Country-Cornerstone-Retreat-Upstairs.h122099546.Hotel-Information) Hillsboro CA $328 CA $373 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Lynchburg-Hotels-Country-Cornerstone-Retreat-Upstairs.h122099546.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/20831dc9.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) ![TV, foosball, stereo](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/33289191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage [](https://www.expedia.ca/Hillsboro-Hotels-Country-Cornerstone-Retreat.h115554816.Hotel-Information) Hillsboro 10/10 Exceptional (2) "The property was perfect for our family weekend getaway. The game room, massage chairs, theater room and hot tub were huge hits. The house was very well stocked with everything we needed to cook full meals. Keith answered every question we had promptly and they had planned for everything including a spare coffee maker when the primary one didn’t work. It’s secluded and quiet for restful and relaxing time away. There was even a on site charger for our EV. We would definitely stay again!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $483 CA $981 total includes taxes & fees Dec 23 - Dec 24 [](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=2025-12-25&endDate=2025-12-26®ionId=183815&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America®ionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America®ionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America®ionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America®ionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=VACATION_HOME) ![](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 ![Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !](https://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 "Cabin was nice and clean and well stocked. Loved that all rooms are on the same level." [](https://expedia.ca/Hillsboro-Hotels-Newly-Built-Rustic-3-Bedroom-Cabin-With-A-One-Acre-Fishing-Lake.h29913121.Hotel-Information) ![Brown's Motel Aberdeen](https://images.trvl-media.com/lodging/11000000/10260000/10253500/10253418/4ca9fc0f_y.jpg) ### Brown's Motel Aberdeen 10/10 Excellent "Rooms where very clean and nice staff was amazing " [](https://expedia.ca/Hillsboro-Hotels-Browns-Motel-Aberdeen.h10253418.Hotel-Information) ![Quality Inn Seaman](https://images.trvl-media.com/lodging/1000000/50000/42800/42751/def57d46_y.jpg) ### Quality Inn Seaman 8/10 Good "Staff very polite. The rail in the shower was loose but i had forgotten to mention it when there. No other issues." [](https://expedia.ca/Hillsboro-Hotels-Quality-Inn.h42751.Hotel-Information) ![Beverly hills inn](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418_y.jpg) ### Beverly hills inn 10/10 Excellent "Perfect place " [](https://expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information) ![Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/3d0b43d9_y.jpg) ### Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio 10/10 Excellent "Very welcoming, clean and very good communicatio." [](https://expedia.ca/Hillsboro-Hotels-Cozy-Meadowview-Guest-House-1-Bedroom-Studio-5-Minutes-To-Downtown-Hillsboro.h90764643.Hotel-Information) ![Paragon Inn Hillsboro](https://images.trvl-media.com/lodging/3000000/2980000/2974700/2974636/8a89f8e6_y.jpg) ### Paragon Inn Hillsboro 10/10 Excellent "Room was exactly as pictured. Clean, no odors, and very pleased! Thank you so much!" [](https://expedia.ca/Hillsboro-Hotels-Paragon-Inn-Hillsboro.h2974636.Hotel-Information) ![Super 8 by Wyndham Maysville KY](https://images.trvl-media.com/lodging/1000000/50000/49900/49881/e877f7ea_y.jpg) ### Super 8 by Wyndham Maysville KY 10/10 Excellent "Staff was nice " [](https://expedia.ca/Maysville-Hotels-Super-8-By-Wyndham-Maysville-KY.h49881.Hotel-Information) ![Days Inn by Wyndham Maysville Kentucky](https://images.trvl-media.com/lodging/1000000/30000/25500/25466/032fdf94_y.jpg) ### Days Inn by Wyndham Maysville Kentucky 10/10 Excellent "Yes the room where very clean and the staff was great " [](https://expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information) ![Quality Inn Maysville](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/5a32ce9b_y.jpg) ### Quality Inn Maysville 10/10 Excellent "Ty" [](https://expedia.ca/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 69 | | ----------------- | ----------------- | | Accommodation | 49 Vacation Homes | | Lowest Price | CA $311 | | Highest Price | CA $981 | ## Explore a world of travel with Expedia - 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