Title: Winchester Chalets from CA $349 | 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) # Search Chalets in Winchester from CA $349 - ![](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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&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) In one month [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) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Chalets ![Exterior](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/20ad081c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/6b12a061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/7d97a0f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/87840bd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-Friendly w Hot Tub, Fire Pit & River Access Great Cacapon 9.4/10 Exceptional (3) "Everything from beginning to end was what we hoped for. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet G. CA $207 CA $404 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Great-Cacapon-Hotels-Dog-Friendly-W-Woodstove.h112655526.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/1ea14aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/de547988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/d247b2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/w1800h1180x0y23-33f4a91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy w Hot Tub, Fire Pit, Wifi, Grill, Deck & Pets Rio 9.0/10 Wonderful (4) "The property was clean and comfortable, had everything we needed. Quiet and peaceful. Hit tub was great. Hope to come back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise S. CA $190 CA $349 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Rio-Hotels-Cozy-W-Hot-Tub.h113684040.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107330000/107324700/107324655/0d253a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107330000/107324700/107324655/7ec3fb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/108000000/107330000/107324700/107324655/8946c843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107330000/107324700/107324655/d84bce1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Fire Pit, Deck, Grill w Resort Amenities The Woods 8.8/10 Excellent (3) "Just stayed overnight. Nicely decorated with not too much stuff I needed to be worried about the kids breaking. I was a little miffed that there's a decent cleaning fee but I had to take the garbage with me. ? Also learned that if I'm expecting to use a feature of a property I should check first to see if it's available - the lighter was dead anywhere were no matches so I had to get mmy own. The firewood that is stored under the " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca W. CA $207 CA $404 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Hedgesville-Hotels-Hot-Tub.h107324655.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114200000/114199900/114199873/7139f299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114200000/114199900/114199873/d9ccd797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/115000000/114200000/114199900/114199873/518f3fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114200000/114199900/114199873/d76fea53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin: Wraparound Deck, WiFi, Grill, Dog-Friendly! Berkeley Springs 10/10 Exceptional (2) "The cabin was a perfect quiet spot to enjoy family time. It was expertly stocked to cook, sleep lots of people, and keep kids entertained. I highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie K. CA $224 CA $460 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Surrounded-By-Nature.h114199873.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76380000/76378300/76378255/3449363f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76380000/76378300/76378255/a4e216f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76380000/76378300/76378255/f45e516d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76380000/76378300/76378255/64cd7ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly Gerrardstown 9.4/10 Exceptional (11) "Perfect quick night away as a family! Especially enjoyed the hot tub!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly L. CA $224 CA $388 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Gerrardstown-Hotels-Modern-Chalet-Cabin-W-Fire-Pit.h76378255.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/4fa2d3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/151b7991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/dfb9bffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/91782102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Access, Loft, Deck, WiFI & Pet Friendly Great Cacapon 10/10 Exceptional (3) "Cabin was very clean and offered many sleeping areas. It was pet friendly although a fenced backyard would be nice. The flashlight located in the hallway was most helpful when letting them out at night. I would place a sign in the shower about pulling the ring down to get the water to come out through the shower. The window unit air conditioners were adequate for a June visit but probably not July or August. I was never able to receive the manual in my email. The key boxes should have the same... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leigh D. CA $223 CA $440 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Great-Cacapon-Hotels-River-Access.h111435023.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92010000/92006600/92006510/f8e84546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92010000/92006600/92006510/ed0a078c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/93000000/92010000/92006600/92006510/371bfb9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92010000/92006600/92006510/277a25f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV. The Woods 9.8/10 Exceptional (19) "House was great and cozy for the family for a weekend away. Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brooke R. CA $239 CA $547 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hedgesville-Hotels-Starcatcher.h92006510.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106860000/106858200/106858150/fbb4f324.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/107000000/106860000/106858200/106858150/63d3b8d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/107000000/106860000/106858200/106858150/ff757e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106860000/106858200/106858150/a49f0e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet w Hot Tub, Fire Pit, Grill & Deck Luray 7.4/10 Good (3) "Overall the stay was pretty mid. The cabin was not as secluded as advertised. The cabin itself was very hot and the first night was unbearable even with the window unit ac exclusive to the living room. The host did provide fans for the rest of the stay. The shower head in the main bathroom is broken and the oven door cannot be opened as it hits a knob for an adjacent cabinet. There was not adequate towels provided for the stay, particularly as there is a hot tub. Overall it met our needs as we... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron F. CA $219 CA $429 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Luray-Hotels-Chalet-W-Hot-Tub.h106858150.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114140000/114131700/114131700/06fd0f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/115000000/114140000/114131700/114131700/3e6cf193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114140000/114131700/114131700/6f55ae44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/115000000/114140000/114131700/114131700/c67b7bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Bedroom Suites, Hot Tub, Jacuzzi Tub & Game Room Berkeley Springs 10/10 Exceptional (1) "Gorgeous spacious clean home with peaceful atmosphere great communication with property manager. We had a wonderful stay. Zero complaints! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie H. CA $260 CA $797 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Berkeley-Springs-Hotels-5-Bedroom-Suites.h114131700.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91820000/91813400/91813389/w2041h1366x0y0-2680f5a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/92000000/91820000/91813400/91813389/6186dd07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91820000/91813400/91813389/8e27ae6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91820000/91813400/91813389/69d00d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Cabin w Hot Tub, Wifi & Huge Deck! Sleepy Hollow 10/10 Exceptional (13) "House was comfortable, the hot tube was relaxing, and the scenery was beautiful. What else do we need?" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd W. CA $207 CA $355 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Hedgesville-Hotels-Modern-Cabin-W-Hot-Tub.h91813389.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105650000/105649100/105649038/w3000h2008x0y0-bf30339c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105649100/105649038/w3000h2000x0y0-8c29bfa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105650000/105649100/105649038/w2733h1534x0y0-b80d3d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105649100/105649038/w2997h2001x0y0-addebb15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Access Cabin w Hot Tub, Grill, Firepit, WiFi Luray 8.6/10 Excellent (11) "Clean and perfect for a short weekend trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khalid S. CA $211 CA $414 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Luray-Hotels-River-Access-Cabin-W-Hot-Tub.h105649038.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120050000/120049400/120049399/9d4cbe9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120050000/120049400/120049399/02e90b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120050000/120049400/120049399/8facb656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120050000/120049400/120049399/2aa5c0c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat w/Hot Tub & Fire Pit near Bryce Mount Jackson 10/10 Exceptional (1) "Great property manager support. Clean and well stocked. Hot tub was well maintained and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John L. CA $224 CA $455 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Mount-Jackson-Hotels-Cozy-Retreat-W-Hot-Tub.h120049399.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105340000/105338100/105338034/8e0b3dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/106000000/105340000/105338100/105338034/7706d529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/106000000/105340000/105338100/105338034/d3985183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/106000000/105340000/105338100/105338034/3d941171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet Cabin w Hot Tub, WiFi, Firepit, Grill, Deck The Woods 9.2/10 Wonderful (5) "Great location for a family getaway to the great outdoors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric H. CA $280 CA $440 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Hedgesville-Hotels-Chalet-Cabin-W-Hot-Tub.h105338034.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100340000/100332200/100332123/dfd504df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100340000/100332200/100332123/dc3e293b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100340000/100332200/100332123/ed267cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100340000/100332200/100332123/aea51f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet Loft Chalet near Bryce w/Hot Tub & Fire Pit Mount Jackson 7.8/10 Good (7) "A good spot in a somewhat secluded neighborhood. The cabin was well furnished, ample space to cook. The location and directions were easy to follow. The hot-tub was available. Host was quick to respond. The house is in the middle of a hilly community" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan M. CA $207 CA $404 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Mount-Jackson-Hotels-Quiet-Wooded-Chalet-Near-Bryce-W-Hot-Tub.h100332123.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/3b07aeb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/584bacd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/1073561a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/f9e8a15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Cabin w Hot Tub, Fire Pit, Deck & Grill! Mount Jackson 8.8/10 Excellent (28) "Can't wait till next year I'm going to the same place again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Archie J. CA $207 CA $351 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Mount-Jackson-Hotels-Creekside-Cabin-W-Hot-Tub.h92356628.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/9816db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo, offices](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/d60aa737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/4338dc74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/cfa84632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern w Mountain Views, Hot Tub, Deck & Fire Pit Berkeley Springs 9.6/10 Exceptional (9) "We enjoyed are us time in this lovely cabin. It was very clean and the hot tub was amazing. It was a very quiet relaxing get away. We definitely recommend this cabin and will hopefully visit again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deeanna C. CA $207 CA $355 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Modern-Cabin-W-Mountain-View.h95585199.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110800000/110798500/110798455/31c4d66b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110800000/110798500/110798455/85d626cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110800000/110798500/110798455/98bae621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110800000/110798500/110798455/9d4c8ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountainside w/Fireplace, Fire Pit, Deck, & WiFi Berkeley Springs 10/10 Exceptional (1) "Cabin is very cozy! We were impressed with how well stocked it as well. 7 adults stayed and we were very comfortable. Also a personal item was left behind and the property manager/cleaning crew were very helpful with communicating this and returning it to us. We felt very taken care of - highly recommend!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret T. CA $354 CA $727 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Mountainside-W-Fireplace.h110798455.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/df219c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/b1e90ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/bc2bc4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/4b3e4419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI Harpers Ferry 9.4/10 Exceptional (27) "We had a great stay and the house was perfect for a quick getaway weekend for our family. Close to wineries and explored Harper’s Ferry. Communication with the host Tony was great. We would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha W. CA $301 CA $509 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Harpers-Ferry-Cabin-W-Hot-Tub.h92168268.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104990000/104985900/104985855/509bcd93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104990000/104985900/104985855/757b8ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo, offices](https://images.trvl-media.com/lodging/105000000/104990000/104985900/104985855/403e8129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo, offices](https://images.trvl-media.com/lodging/105000000/104990000/104985900/104985855/d4d5e4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet w Hot Tub, Grill, FirePit, WiFi,PetFriendly Berkeley Springs 10/10 Exceptional (2) "Wonderful place, peaceful and quiet. Very clean!! Didn't have to travel to far if we wanted to find things to do.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie S. CA $208 CA $355 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Chalet-W-Hot-Tub.h104985855.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435019/c4d73ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435019/cccc623e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435019/f069ebf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435019/63920673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loft, Wood Stove, Fire Pit, Grill & Deck on Creek Hedgesville 10/10 Exceptional (6) "Wonderful place to stay for a girls weekend away! Hosts were accessible and very good communication throughout the stay. We saw two deer stroll by the house and had a visit from a possum when we had a camp fire. :-) Enjoyed our time for sure! Thank you - Jessica" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica and Kevin C. CA $258 CA $526 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Loft.h111435019.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=2025-11-19&endDate=2025-11-20®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-Chalets.d6056879-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Chalets.d6056879-aaChalets.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![TRU By Hilton Winchester](//images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Gentleman who checked us in was friendly and welcoming and put a smile on our faces. Breakfast is your typical Hotel breakfast." [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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 "good breakfast and service. room felt a bit cramped and tv did not work " [](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 "Clean. Comfortable. Nice staff. Breakfast was good. " [](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 "XXXX" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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 "Very pleasant and right off the interstate " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Hampton Inn Winchester N/Conference Center, VA](//images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg) ### Hampton Inn Winchester N/Conference Center, VA 10/10 Excellent "The room was lovely. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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 "The room was clean. The staff were courteous. Everything at this hotel was top notch. One of the best hotel stays I've had in a long time." [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Quality Inn Winchester](//images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Clerk was very friendly! Room was clean. Loved that Dennys was so convenient! Have stayed here twice and very pleased with both stays. " [](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 "Service was great!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Find out more about Winchester ## Winchester Chalets information | Number of reviews | 142 | | --- | --- | | Accommodation | 67 Chalets | | Lowest Price | CA $349 | | Highest Price | CA $797 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - [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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[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)