Title: Winchester Vacation Home Rentals from CA $248: 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 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/32a5f0df.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 " CA $189 CA $309 total includes taxes & fees Oct 14 - Oct 15 [](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) ![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.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 (36) "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. " CA $224 CA $457 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.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) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/cbf483db.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) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/1ca53946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cameron Charmer pristine downtown apt with double master suites Winchester 9.4/10 Exceptional (3) "Nice house in a good central location. " CA $277 CA $492 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.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) ![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) ![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/9221f31b.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) ### 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!" CA $237 CA $424 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.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) ![Exterior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/acaffbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/ed3d2da3.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) ### 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. " CA $258 CA $643 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/w1184h883x3y0-95d19d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries Linden 10/10 Exceptional (17) "View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. " CA $192 CA $409 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.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) ![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) ![TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/93000000/92570000/92563800/92563765/f787795e.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!!!" CA $1,261 CA $2,017 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Front-Royal-Hotels-Pirates-Cove-River-Front-Oasis.h92563765.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. " CA $255 CA $579 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/25a6efcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/563df015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/a2c39a40.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) ### The Apple Mountain House Front Royal 9.6/10 Exceptional (5) "Amazing place to relax." CA $242 CA $615 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.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) ![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/c61d77dc.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/ccb9b8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Sunny Family House Front Royal 10/10 Exceptional (37) "This is our second time staying here, lots of room and great communication!" CA $293 CA $680 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.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) ![Dining](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/de9610ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/w1320h979x0y0-b14f5b87.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 $1,191 CA $1,536 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.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) ![Interior](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/6278c5db.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) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/c04a2393.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 CA $401 CA $760 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Linden-Hotels-Cozy-Luxury.h118355581.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) ![Interior](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w301h683x362y0-55da1602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100460000/100457800/100457711/w904h683x60y0-d58dc19c.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) ### Primitive Cozy off grid tiny home with Starlink Great Cacapon 9.8/10 Exceptional (9) "Awesome spot. Highly recommend. " CA $101 CA $260 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Great-Cacapon-Hotels-Primitive-Cozy-Off-Grid-Tiny-Home-With-Starlink.h100457711.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/257ce76b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/4a85b170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121240000/121236000/121235959/29c48c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](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 $153 CA $323 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Martinsburg-Hotels-Pleasant-3-Bedroom-House-With-AC-In-Martinsburg.h121235959.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) ![Outdoor dining](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/046a30f4.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 9.4/10 Exceptional (10) "We liked being out in the country. Loved hearing the sounds of the woods and the farms. Lovely spot" CA $139 CA $301 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Edinburg-Hotels-Peaceful-Retreat-On-Creekside.h97582140.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/beb9f8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/630d5570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/0a99747a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/f0a9c087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes! Harpers Ferry 10/10 Exceptional (5) CA $175 CA $508 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.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) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h1720x0y7-db264944.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) ![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) ### Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres! Rixeyville 10/10 Exceptional (3) "Great little place. Perfect for one or two travelers.Super nice hosts. Would highly recommend." CA $125 CA $311 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/de23b91c.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) ![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! " CA $161 CA $334 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) ![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) ![Living area](https://images.trvl-media.com/lodging/96000000/95480000/95476100/95476079/w905h683x60y0-d5d74521.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) ### Kalia’s Mountain Momma Getaway Harpers Ferry 10/10 Exceptional (11) "Location was nice" CA $153 CA $248 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Kalias-Mountain-Momma-Getaway.h95476079.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107010000/107002500/107002436/22db01ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107002500/107002436/2327d874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/108000000/107010000/107002500/107002436/58e0709d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107002500/107002436/439d55cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anne's Retreat Luray 10/10 Exceptional (3) "Great location for hiking. Had everything we needed. " CA $221 CA $728 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Luray-Hotels-Annes-Retreat.h107002436.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=2025-10-26&endDate=2025-10-27®ionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 ![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 "Great stay! Would definitely would stay again!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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 "I love this place. Very clean. I've been to many motels in the area and they are horrible, filthy, unkempt properties. Here they have an elevator which is very easy on the legs and arms when getting one's luggage in. Very congenial owner. They don't discriminate against smokers. Other motels in the area put a smoker in rooms that weren't even cleaned. I would recommend this Travel Lodge to all types of guests. Business or leisure." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Staff was outstanding and very helpful with a thorny situation " [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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 "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![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 "Convenient " [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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 "Great location." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean place good price" [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 "Always da best motel an experience " [](https://expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 207 | | --- | --- | | Accommodation | 619 Vacation Homes | | Lowest Price | CA $248 | | Highest Price | CA $2,036 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - 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