Title: Winchester Vacation Home Rentals from CA $247: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.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=6056879&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=6056879&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=6056879&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=6056879&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 ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/ab6df544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/282cc197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/cb8a9693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/abe2d599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries Linden 10/10 Exceptional (18) "View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew G. CA $161 CA $371 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/928d407e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Bungalow in Front Royal Front Royal 10/10 Exceptional (4) "Property was just what we were looking for " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim C. CA $189 CA $310 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/15fd4469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/bc1a175e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/2f2ce964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/8e6ba5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly renovated Farm cottage with Mountain views Strasburg 10/10 Exceptional (37) "Very clean cottage with well-stocked kitchen with a great outdoors area for grilling and hanging out. Quiet relaxing location way up off the road. The hosts were unobtrusive but available. We have already recommended this cottage to our immediate family for future stays. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Becky C. CA $224 CA $455 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/13764d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/9641cad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/acaffbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/a696274d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bluemont Village Home Bluemont 10/10 Exceptional (36) "No need to look any further! Beautiful, clean,historic home in a perfect location. Close to wineries, breweries, Shenandoah River, hiking and only 45 minutes from DC. The host was very accommodating and friendly as well. We would highly recommend this home for you and your family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian and Allison W. CA $220 CA $599 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x1y1-de179e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2998h2002x1y1-e4dac9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x0y1-34023d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w3000h2002x0y1-874ebd45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcome to the Ladybug Retreat! Boyce 10/10 Exceptional (1) "This home is lovely and the host has thought of everything. We will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine A. CA $245 CA $566 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/4d7efd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/ea0185a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/2032cec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/25a6efcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Apple Mountain House Front Royal 9.8/10 Exceptional (6) "Amazing place to relax." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edna K. CA $183 CA $542 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/a448a4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/7966de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/9221f31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/73acc693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom! Front Royal 9.0/10 Wonderful (26) "Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shugie B. CA $237 CA $423 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/a4ec224c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/6b5ccc9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/cbf483db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/396388c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cameron Charmer pristine downtown apt with double master suites Winchester 9.6/10 Exceptional (4) "The home was exactly as advertised! It was also located in a great spot whichbwas within walking distance to many of the Historic District of Downtown Winchester. We will definitely be staying here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David K. CA $277 CA $491 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/2736c2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, stovetop](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/93b157cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/7a491c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/ef522d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Riverfront Home Getaway with Hot Tub Warren County CA $279 CA $646 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/23f46f24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/43d2da0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/b0176d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/ccb9b8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Sunny Family House Front Royal 10/10 Exceptional (38) "This is our second time staying here, lots of room and great communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katelyn W. CA $266 CA $646 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92570000/92563800/92563765/8791fe08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/93000000/92570000/92563800/92563765/a9cdc921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/93000000/92570000/92563800/92563765/ca4faffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92563800/92563765/9dc859e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pirate's Cove River Front Oasis, Group Adventure Warren County 10/10 Exceptional (4) "The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassie A. CA $1,259 CA $2,012 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Front-Royal-Hotels-Pirates-Cove-River-Front-Oasis.h92563765.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/88000000/87700000/87693600/87693549/cecf4c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87700000/87693600/87693549/e0654697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87700000/87693600/87693549/d8efd7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87700000/87693600/87693549/c2718ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On the river ~ hot tub ~ serene river views ~ fire pit Strasburg 10/10 Exceptional (25) "We enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madeleine K. CA $373 CA $725 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Strasburg-Hotels-On-The-River-Serene-Views-Fire-Pit.h87693549.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/88fd6b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/c54a2943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/25a34129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/6278c5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA Linden 10/10 Exceptional (1) "This place was very nice and well equipped with everything that you would need. It was very clean, quiet and had plenty of space. This is a great place to stay if you're in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael C. CA $400 CA $764 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Linden-Hotels-Cozy-Luxury.h118355581.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/512057d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/89b2ef24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/de9610ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/df4a0d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Front royal majestic paradise Front Royal CA $1,398 CA $1,822 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w907h683x58y0-b210240b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w526h683x258y0-cf23250b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w301h683x362y0-55da1602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w905h683x59y0-a003152e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Primitive Cozy off grid tiny home with Starlink Great Cacapon 9.8/10 Exceptional (9) "Awesome spot. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory M. CA $101 CA $260 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Great-Cacapon-Hotels-Primitive-Cozy-Off-Grid-Tiny-Home-With-Starlink.h100457711.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/3fb8f14c_edited_6688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h968x0y3-80f99c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h2284x0y0-8ada8d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h982x0y0-a74e1c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres! Rixeyville 10/10 Exceptional (4) "Great place. Great people!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $125 CA $318 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Rixeyville-Hotels-Charming-1-Bedroom-House-With-WiFi.h112761217.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/354e36e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/57cbb436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/dbbf789b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/529562ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park Luray 10/10 Exceptional (10) "Great stay- only one night for a friends wedding in Shenandoah. Nice place to stay, no issues! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelin S. CA $161 CA $339 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Luray-Hotels-Peaceful-Cottage-In-Farmland-4-Miles-To-Luray9-Miles-To-ShenNatl-Park.h106262808.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/d64b9ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/611a040d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/95da1211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/1db4e449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Retreat on Creekside Edinburg 9.6/10 Exceptional (11) "We liked being out in the country. Loved hearing the sounds of the woods and the farms. Lovely spot" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $138 CA $304 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Edinburg-Hotels-Peaceful-Retreat-On-Creekside.h97582140.Hotel-Information) ![Dining tables](https://images.trvl-media.com/lodging/96000000/95480000/95476100/95476079/w905h683x60y0-69cd861e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95480000/95476100/95476079/w525h683x259y0-986db5cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95480000/95476100/95476079/w905h683x60y0-6c1fca10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/96000000/95480000/95476100/95476079/w904h683x60y0-62dfd450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kalia’s Mountain Momma Getaway Harpers Ferry 10/10 Exceptional (11) "Location was nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $152 CA $247 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Kalias-Mountain-Momma-Getaway.h95476079.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/434a02e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/4aed0284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/d6aa9b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/5fb27894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant 3-bedroom house with AC in Martinsburg Martinsburg CA $152 CA $328 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Martinsburg-Hotels-Pleasant-3-Bedroom-House-With-AC-In-Martinsburg.h121235959.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=6056879&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.d6056879-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.d6056879-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![SpringHill Suites by Marriott Winchester](//images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Fantastic from start to finish." [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Good" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Clean rooms and comfortable beds and bedding. Plentiful bath towels. Convenient location " [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Quality Inn Winchester](//images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Yes" [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Amazing hotel with lovely rooms, easy parking, near (walking distance ) great restaurants and shops. Highly recommend spa in building." [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "New contemporary hotel; comfortable bed and nicely decorated room. Good location to restaurants and the highway. Nice staff and good breakfast (standard food items). Only complaint is that need a few more parking spaces. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Motel 6 Winchester, VA](//images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676_y.jpg) ### Motel 6 Winchester, VA 10/10 Excellent "Very clean, safe. " [](https://expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean room. Good breakfast" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Parking area felt very safe. Fruit available for breakfast. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 233 | | --- | --- | | Accommodation | 619 Vacation Homes | | Lowest Price | CA $247 | | Highest Price | CA $2,012 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Luxury-Hotel.0-0-d184082-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights to Millwood](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Gore](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Visit Millwood](https://www.expedia.ca/Millwood.dx3000460156) - [Book Vacation Homes in Winchester on Expedia.com](https://www.expedia.com/Winchester-Private-Vacation-Homes.d6056879-aaPrivateVacationHomes.Travel-Guide-Accommodation)