Title: Winchester Chalets from CA $345 | 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 $345 ![](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=CHALET&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=CHALET&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=CHALET&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=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Chalets ![Property grounds](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/654306d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/0a85581d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/10bb3434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/001a3838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries Bluemont 10/10 Exceptional (1) "Perfect escape/getaway!!! Beautiful surroundings, beautiful decor and super clean. The home has everything available if you never want to leave the premises. Hot tub, sauna, cold plunge, fire pit, grill and Zen Den made this an easy decision to book. 5 Stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison K. CA $443 CA $943 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bluemont-Hotels-Emberwood-Modern-Chalet-Nature-Spa-Trails.h118168351.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/83c72003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113690000/113684100/113684040/18026e27.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/114000000/113690000/113684100/113684040/8bfc36fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy w Hot Tub, Fire Pit, Wifi, Grill, Deck & Pets Rio 9.4/10 Exceptional (3) "Clean, comfortable cabin, and very effective communication from the host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keely CA $190 CA $345 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Rio-Hotels-Cozy-W-Hot-Tub.h113684040.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/115000000/114140000/114131700/114131700/6f55ae44.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) ### 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. [](https://www.expedia.ca/Berkeley-Springs-Hotels-5-Bedroom-Suites.h114131700.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) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/108000000/107330000/107324700/107324655/002e25ec.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) ### Hot Tub, Fire Pit, Deck, Grill w Resort Amenities The Woods 8.8/10 Excellent (3) "Great stay! Peaceful and quiet area! Everything was wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen C. CA $207 CA $404 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hedgesville-Hotels-Hot-Tub.h107324655.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110988600/110988526/14360f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110988600/110988526/07d0c1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110988600/110988526/996f17ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110988600/110988526/914d3903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy w Fire Pit, Deck, Screened Porch & WiFi Harpers Ferry 10/10 Exceptional (1) "Our family had a cozy weekend at the cabin. Tony was super helpful and a great host. Thank you for sharing your lovely property with us!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katrina S. CA $237 CA $446 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Cozy-W-Fire-Pit.h110988526.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/20ad081c.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112660000/112655600/112655526/e0037060.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) ### Dog-Friendly w Hot Tub, Fire Pit & River Access Great Cacapon 9.4/10 Exceptional (3) "Very fun stay, very clean. Beautiful weather for walking around the place. Would definitely come back!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deepan R. CA $207 CA $403 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Great-Cacapon-Hotels-Dog-Friendly-W-Woodstove.h112655526.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107090000/107086100/107086064/e6b1dad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107090000/107086100/107086064/459c0bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107090000/107086100/107086064/7577abfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107090000/107086100/107086064/9de42190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin w Hot Tub, WiFi, Deck, Grill & Dog-Friendly! Berkeley Springs 9.6/10 Exceptional (5) "Had a good time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tessa E. CA $255 CA $485 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Cabin-W-Hot-Tub.h107086064.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) ![Dining](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/f9e8a15d.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) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92356700/92356628/b26c41a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Cabin w Hot Tub, Fire Pit, Deck & Grill! Mount Jackson 8.6/10 Excellent (27) "Was exactly what we were looking for. Isolated, beautiful area, nice washer & dryer, wifi, hot tub. Hope to come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert C. CA $207 CA $350 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Mount-Jackson-Hotels-Creekside-Cabin-W-Hot-Tub.h92356628.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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/7179087c.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) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111440000/111435100/111435023/151b7991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Access, Loft, Deck, WiFI & Pet Friendly Great Cacapon 10/10 Exceptional (3) "Loved the place and the secluded mountain setting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) melissa w. CA $222 CA $442 total includes taxes & fees Oct 26 - Oct 27 [](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/ee450ddd.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) ### This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV. The Woods 9.8/10 Exceptional (19) "Plenty of amenities with the resort/spa very close to make for a wonderful family getaway weekend trip. Or just staying at the cabin also full of things to do for all ages!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana H. CA $238 CA $543 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hedgesville-Hotels-Starcatcher.h92006510.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) ![Exterior](https://images.trvl-media.com/lodging/115000000/114200000/114199900/114199873/deaec097.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) ### Cabin: Wraparound Deck, WiFi, Grill, Dog-Friendly! Berkeley Springs 10/10 Exceptional (2) "The house was exactly as it looked in the pictures. It was stocked with everything we needed and was very clean. Very quiet location and easy to get to. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie M. CA $223 CA $461 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Surrounded-By-Nature.h114199873.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) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/92000000/91820000/91813400/91813389/3e1d87a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Cabin w Hot Tub, Wifi & Huge Deck! Sleepy Hollow 10/10 Exceptional (12) "Very peaceful , quiet , and cozy. Grill, Hot tub , & fire pit were great! Had a nice stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis S. CA $237 CA $393 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hedgesville-Hotels-Modern-Cabin-W-Hot-Tub.h91813389.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/77000000/76380000/76378300/76378255/64cd7ac3.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) ### Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly Gerrardstown 9.4/10 Exceptional (11) "We had a fabulous time and highly recommend this rental." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amber H. CA $244 CA $413 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Gerrardstown-Hotels-Modern-Chalet-Cabin-W-Fire-Pit.h76378255.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/31000000/30330000/30327000/30326974/w799h599x1y1-834cab7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/31000000/30330000/30327000/30326974/48a944f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/31000000/30330000/30327000/30326974/cbc7bbee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30330000/30327000/30326974/6949acb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded,Mountain View, House, Hot tub, Wifi, King beds, Near Cacapon State Park Berkeley Springs 10/10 Exceptional (272) "Place was great, kids had alot of fun. Host was very informative and great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kara I. CA $252 CA $874 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Martinsburg-Hotels-Secluded.h30326974.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) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105649100/105649038/f8c39a60.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) ### River Access Cabin w Hot Tub, Grill, Firepit, WiFi Luray 8.6/10 Excellent (11) "We had a great time staying here and using the house as a base for hiking. The kids loved the football table and the hot tub was clean and hot!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Rebecca S. CA $230 CA $437 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Luray-Hotels-River-Access-Cabin-W-Hot-Tub.h105649038.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) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/cfa84632.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) ![TV, books, stereo, offices](https://images.trvl-media.com/lodging/96000000/95590000/95585200/95585199/5d0de6c2.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) "Loved the hot tub and fire pit. Dogs enjoyed the secluded property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean R. CA $237 CA $392 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Modern-Cabin-W-Mountain-View.h95585199.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76130000/76120600/76120586/c123ce4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76130000/76120600/76120586/3b45b8da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76130000/76120600/76120586/87dee70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76130000/76120600/76120586/1bf27a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Chalet w Hot Tub, Large Deck, Grill & WiFi Gerrardstown 9.6/10 Exceptional (5) "Just an overnight stay. On our way back home from northern New York. The place was nice. It is peaceful sitting on the deck. The check in process was a little tedious with various emails and downloads required. The Backstep is a little sketchy. Be careful walking in. Overall the place was nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John Z. CA $207 CA $367 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Gerrardstown-Hotels-Secluded-Chalet-Cabin-W-DeckGrill.h76120586.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100340000/100332200/100332123/60571ffa.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 Oct 29 - Oct 30 [](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/77000000/76900000/76891000/76890990/92da9e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/77000000/76900000/76891000/76890990/f9354717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/77000000/76900000/76891000/76890990/ebf7692c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76900000/76891000/76890990/12c16936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountaintop Views, Hot Tub, Deck, Fire Pit & WiFi Augusta 9.6/10 Exceptional (14) "Loved the beautiful scenery and location. Very peaceful and relaxing. Just what we were looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mindy R. CA $259 CA $436 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Augusta-Hotels-Mountaintop-Chalet-W-Amazing-Views.h76890990.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/106000000/105340000/105338100/105338034/3d941171.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) ### Chalet Cabin w Hot Tub, WiFi, Firepit, Grill, Deck The Woods 9.2/10 Wonderful (5) "Great place to stay with decent space. Overall good vibes " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan S. CA $301 CA $468 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Hedgesville-Hotels-Chalet-Cabin-W-Hot-Tub.h105338034.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=2025-11-05&endDate=2025-11-06®ionId=6056879&adults=2&lodging=CHALET&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-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 ![Candlewood Suites Winchester by IHG](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg) ### Candlewood Suites Winchester by IHG 10/10 Excellent "Megan is delightful" [](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.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 "It was great the only thing bad .Breakfast only started at 7 am we had to leave at 6.30 am" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 staff ws wonderful. Very clean" [](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 "Staff was super friendly and accommodating " [](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 "Wonderful stay. " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 "Convenient location, clean, reasonable price" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 "Great little hotel if of I81. Very friendly staff and streamlined service. Darci was exceptional. Rooms are small but very nicely appointed and clean. Hot coffee in the lobby when we arrived. Decent breakfast. Indoor pool and fitness center. Definitely recommend. " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Spark by Hilton Winchester](//images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg) ### Spark by Hilton Winchester 10/10 Excellent "Worked for me" [](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![TRU By Hilton Winchester](//images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Nice and clean spot with good Lavazza coffee at all hours. The breakfast selection were surprisingly nice. Good spot." [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ## Find out more about Winchester ## Winchester Chalets information | Number of reviews | 375 | | --- | --- | | Accommodation | 67 Chalets | | Lowest Price | CA $345 | | Highest Price | CA $943 | ## 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) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Inns in Berryville](https://www.expedia.ca/Berryville-Inns.d184082-aaInns.Travel-Guide-Accommodation) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Boyce](https://www.expedia.ca/Boyce-Hotels-Boutique-Hotel.0-0-d184084-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Boyce Hotels](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [Motels in Boyce](https://www.expedia.ca/Boyce-Motels.d184084-aaMotels.Travel-Guide-Accommodation) - [Hotels near Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [Motels in Brucetown](https://www.expedia.ca/Brucetown-Motels.d3000355042-aaMotels.Travel-Guide-Accommodation) - [Cheap Hotels in Clear Brook](https://www.expedia.ca/Clear-Brook-Hotels-Cheap-Hotels.0-0-d553248635975870250-tCheapHotels.Travel-Guide-Filter-Hotels) - [Clear Brook Hotels](https://www.expedia.ca/Clear-Brook-Hotels.d553248635975870250.Travel-Guide-Hotels) - [B&B in College Park](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Vacation Homes in College Park](https://www.expedia.ca/College-Park-Private-Vacation-Homes.d553248635975870482-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels near Dinosaur Land](https://www.expedia.ca/Dinosaur-Land-Hotels.0-l553248621532661835-0.Travel-Guide-Filter-Hotels) - [B&B in Frederick County](https://www.expedia.ca/Frederick-County-Bed-And-Breakfast.d553248635976431672-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Frederick County](https://www.expedia.ca/Frederick-County-Cottages.d553248635976431672-aaCottages.Travel-Guide-Accommodation) - [Gainesboro Hotels](https://www.expedia.ca/Gainesboro-Hotels.d553248635976006643.Travel-Guide-Hotels) - [Hotels near George Washington's Office](https://www.expedia.ca/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels) - [Farmstay in Gore](https://www.expedia.ca/Gore-Agritourism.d3000460015-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Gore](https://www.expedia.ca/Gore-Bed-And-Breakfast.d3000460015-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Gore](https://www.expedia.ca/Gore-Chalets.d3000460015-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Gore](https://www.expedia.ca/Gore-Guest-Houses.d3000460015-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Gore](https://www.expedia.ca/Gore-Hotels-Cheap-Hotels.0-0-d3000460015-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Gore](https://www.expedia.ca/Gore-Hotels-Luxury-Hotel.0-0-d3000460015-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Gore Hotels](https://www.expedia.ca/Gore-Hotels.d3000460015.Travel-Guide-Hotels) - [Inns in Gore](https://www.expedia.ca/Gore-Inns.d3000460015-aaInns.Travel-Guide-Accommodation) - [Lodges in Gore](https://www.expedia.ca/Gore-Lodges.d3000460015-aaLodges.Travel-Guide-Accommodation) - [B&B in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Bed-And-Breakfast.d553248635975872368-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Cottages.d553248635975872368-aaCottages.Travel-Guide-Accommodation) - [Villas in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Villas.d553248635975872368-aaVillas.Travel-Guide-Accommodation) - [Luxury Hotels in Kernstown](https://www.expedia.ca/Kernstown-Hotels-Luxury-Hotel.0-0-d553248635975850140-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Kernstown Hotels](https://www.expedia.ca/Kernstown-Hotels.d553248635975850140.Travel-Guide-Hotels) - [B&B in Middletown](https://www.expedia.ca/Middletown-Bed-And-Breakfast.d12013-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Inns in Middletown](https://www.expedia.ca/Middletown-Inns.d12013-aaInns.Travel-Guide-Accommodation) - [Motels in Middletown](https://www.expedia.ca/Middletown-Motels.d12013-aaMotels.Travel-Guide-Accommodation) - [Apartments in Millwood](https://www.expedia.ca/Millwood-Apartments.d3000460156-aaApartments.Travel-Guide-Accommodation) - [B&B in Millwood](https://www.expedia.ca/Millwood-Bed-And-Breakfast.d3000460156-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Millwood](https://www.expedia.ca/Millwood-Guest-Houses.d3000460156-aaGuestHouses.Travel-Guide-Accommodation) - [Millwood Hotels](https://www.expedia.ca/Millwood-Hotels.d3000460156.Travel-Guide-Hotels) - [Lodges in Millwood](https://www.expedia.ca/Millwood-Lodges.d3000460156-aaLodges.Travel-Guide-Accommodation) - [Townhomes in Millwood](https://www.expedia.ca/Millwood-Townhomes.d3000460156-aaTownhomes.Travel-Guide-Accommodation) - [Villas in Millwood](https://www.expedia.ca/Millwood-Villas.d3000460156-aaVillas.Travel-Guide-Accommodation) - [Hotels near Mt Hebron Cemetery](https://www.expedia.ca/Mt-Hebron-Cemetery-Hotels.0-l553248621532661845-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Cheap-Hotels.0-n6164092-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Balconies.0-n6164092-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Breakfast.0-n6164092-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Parking.0-n6164092-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Smoking-Rooms.0-n6164092-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Luxury-Hotel.0-n6164092-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Pet-Friendly-Hotel.0-n6164092-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Old Town Winchester Hotels](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Lodges in Riverton](https://www.expedia.ca/Riverton-Lodges.d553248635975849884-aaLodges.Travel-Guide-Accommodation) - [Hotels near Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Cottages in Shawnee Land](https://www.expedia.ca/Shawnee-Land-Cottages.d553248635975849755-aaCottages.Travel-Guide-Accommodation) - [Hotels near Shenandoah University](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [Hotels near State Arboretum of Virginia](https://www.expedia.ca/State-Arboretum-Of-Virginia-Hotels.0-l6164038-0.Travel-Guide-Filter-Hotels) - [B&B in Stephens City](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Pet-Friendly-Hotel.0-0-d12076-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Stephens City Hotels](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels) - [Hotels near Valerie Hill Winery](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in White Post](https://www.expedia.ca/White-Post-Hotels-Honeymoon-Hotels.0-0-d184119-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [White Post Hotels](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [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)