Title: Winchester Cottages from CA $232 | 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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester cottages ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/7f22680b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/d5eb0f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/212d2c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information) Front Royal 10/10 Exceptional (5 reviews) "My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay L. CA $157 CA $507 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain Top hot tub overlooking the Shenandoah River [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) Front Royal 10/10 Exceptional (14 reviews) "We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan P. CA $206 CA $567 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/215d28e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/1920a52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/c495590f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/d6f342ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat - Hot tub + Mountain Views + Pets [](https://www.expedia.ca/Fort-Valley-Hotels-NEW-Mountain-Views-Cottage-Near-Shenandoah.h89671491.Hotel-Information) Fort Valley 9.8/10 Exceptional (61 reviews) "Cute little cottage with beautiful views. The hot tub and fire pit were a great bonus. We will come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul T. CA $121 CA $367 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Fort-Valley-Hotels-NEW-Mountain-Views-Cottage-Near-Shenandoah.h89671491.Hotel-Information) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/3037b62c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/1bc8e0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/bee6d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/51da24ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'thomson Farm' Classic Home < 10 Mi to Vineyards! [](https://www.expedia.ca/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information) Leesburg CA $1,482 CA $2,493 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/5bda07b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/a448d69e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/b5421e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/0ba870a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage by the Caverns \*FIRE PIT\* \*MOUNTAIN VIEWS\* [](https://www.expedia.ca/Luray-Hotels-Cottage-By-The-Caverns-FIRE-PIT-MOUNTAIN-VIEWS.h89626269.Hotel-Information) Luray 9.8/10 Exceptional (84 reviews) "Host was very welcoming and kept me informed throughout the process. They provided recommendations of places to eat and breweries nearby! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John G. CA $196 CA $420 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Luray-Hotels-Cottage-By-The-Caverns-FIRE-PIT-MOUNTAIN-VIEWS.h89626269.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/5b084607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/9314e22d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/467055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/b4f03d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers [](https://www.expedia.ca/Berkeley-Springs-Hotels-Quiet-Cottage-On-Five-Acres-Of-Woods-Close-To-All-That-BerkeleySprings-Offers.h103986494.Hotel-Information) Berkeley Springs 9.4/10 Exceptional (19 reviews) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy C. CA $203 CA $571 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Quiet-Cottage-On-Five-Acres-Of-Woods-Close-To-All-That-BerkeleySprings-Offers.h103986494.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/e475b7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/0861e87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/55bd22b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Docko - Lakefront Artist Retreat w/ Hot Tub! [](https://www.expedia.ca/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information) Harpers Ferry 10/10 Exceptional (23 reviews) "Lovely views, very spacious, well appointed in terms of kitchen." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sharyn m. CA $137 CA $599 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/5709e3b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/346044b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/b18e03f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/5b1052f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Lakefront Cottage with Mountain Views! [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information) Harpers Ferry 10/10 Exceptional (32 reviews) "Great location. Beautiful scenery. House was clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon H. CA $136 CA $501 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/06517d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/76e1ebf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/088a3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/d6f1c9e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs [](https://www.expedia.ca/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information) Harpers Ferry 9.6/10 Exceptional (10 reviews) "We had a great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren O. CA $141 CA $748 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/19e03d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/7bd3216c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/464cb9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/927d6a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage House at Carrot Top Cottage [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Carriage-House-At-Carrot-Top-Cottage.h78111000.Hotel-Information) Harpers Ferry 9.8/10 Exceptional (44 reviews) "The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly W. CA $134 CA $232 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Carriage-House-At-Carrot-Top-Cottage.h78111000.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/ca0816c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/5b26230e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/50e7f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wild Hare Cottage [](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information) Purcellville 10/10 Exceptional (12 reviews) "Loved everything about this location and home - very quiet and charming. Very clean and felt like home. Will definitely visit again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $172 CA $302 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/8e487be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/ba004d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/332db170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/971e942b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing dog-friendly cottage. Walk 2 Harpers Ferry [](https://www.expedia.ca/Harpers-Ferry-Hotels-Amazing-Dog-Friendly-Cottage-Walk-2-Harpers-Ferry.h106001094.Hotel-Information) Harpers Ferry 9.8/10 Exceptional (22 reviews) "Really nice property, and exactly as advertised. There were several local restaurants within easy walking distance (we loved both Bolivar Bread and Snallygaster's) and it was a fairly easy walk to the historic part of Harper's Ferry. We also enjoyed the fire pit in the back yard." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg B. CA $225 CA $415 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Amazing-Dog-Friendly-Cottage-Walk-2-Harpers-Ferry.h106001094.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/8bcbc451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/81983e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/44a70f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/be60aec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake View Retreat - Cottage Near a Peaceful Lake! [](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information) Harpers Ferry 9.6/10 Exceptional (22 reviews) "The house was clean, had plenty of rooms and a fantastic location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan N. CA $136 CA $495 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w508h683x258y0-868506a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w507h683x259y0-14d954d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w508h683x258y0-7f4d529e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w507h683x258y0-4666fb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Waterfall House -- 2 bedroom hidden treasure [](https://www.expedia.ca/Berkeley-Springs-Hotels-Peaceful-Waterfall-House-2-Bedroom-Hidden-Treasure.h101446518.Hotel-Information) Berkeley Springs 9.6/10 Exceptional (10 reviews) "Absolutely our favorite rental by far! Everything was perfect. So very relaxing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine M. CA $274 CA $435 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Berkeley-Springs-Hotels-Peaceful-Waterfall-House-2-Bedroom-Hidden-Treasure.h101446518.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/f515f3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/74329033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/f166d1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/31dbe26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodsy Retreat with a Hot Tub and Seasonal Views! [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information) Harpers Ferry 9.8/10 Exceptional (24 reviews) "I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia F. CA $136 CA $466 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/dd999d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/113b4071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/5b5da494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage w/ Hot Tub and 100-Mile Valley Views! [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information) Harpers Ferry 9.8/10 Exceptional (20 reviews) "Great view, very secluded" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt s. CA $136 CA $515 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/125000000/124350000/124343800/124343763/21a6eb8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124350000/124343800/124343763/9b83c9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124350000/124343800/124343763/w1199h797x155y186-0cd294fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124350000/124343800/124343763/e3e58b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Haven - 3 BR 2.5 Bath Cottage 7 min to Bryce, Spa, Indoor Sauna, Game Room [](https://www.expedia.ca/Mount-Jackson-Hotels-Maple-Haven-3-BR-25-Bath-Cottage-7-Min-To-Bryce.h124343763.Hotel-Information) Mount Jackson CA $219 CA $618 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Mount-Jackson-Hotels-Maple-Haven-3-BR-25-Bath-Cottage-7-Min-To-Bryce.h124343763.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/8d8c27be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/fa7cba31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/068d8c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/682637e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country! [](https://www.expedia.ca/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information) Hamilton 9.6/10 Exceptional (10 reviews) "It was a great place to starve whole experience was perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime B. CA $307 CA $540 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/cc14e518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/98988d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/4f401016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/05617209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal Heritage Home @ Historic Leesburg [](https://www.expedia.ca/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.Hotel-Information) Leesburg's Old and Historic District 9.8/10 Exceptional (39 reviews) "Great location, would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric D S. CA $293 CA $650 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/b94ceda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/0ee9ec99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e29f28d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/661e8116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Century Stone Cottage minutes from historic Middleburg [](https://www.expedia.ca/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information) Middleburg 10/10 Exceptional (55 reviews) "Loved out stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emilee CA $375 CA $542 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.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=2026-02-18&endDate=2026-02-19®ionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CHALET) ![](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-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "The room was spotless , and the staff was very curtis" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Room was very clean and spacious, staff was wonderful!" [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean place, breakfast ok, warm and comfy, would stay again" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Clean nice room Great location for restaurants " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Mimslyn Inn Historic Hotels Of America](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d_y.jpg) ### Mimslyn Inn Historic Hotels Of America 10/10 Excellent "Nice hotel" [](https://expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) ![Candlewood Suites Winchester by IHG](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg) ### Candlewood Suites Winchester by IHG 10/10 Excellent "Staff outstanding and helpful " [](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg) ### Hampton Inn Martinsburg 10/10 Excellent "It was a great experience " [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg) ### Lansdowne Resort and Spa 10/10 Excellent "The resort was in great condition and very clean. The food at Coton & Rye was good for the price. Service throughout the weekend was excellent. " [](https://expedia.ca/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | 500 | | ----------------- | ------------ | | Accommodation | 191 Cottages | | Lowest Price | CA $232 | | Highest Price | CA $2,493 | ## Frequently asked questions ### Why book your cottage in Winchester with Expedia? ### How can I find cheap cottages in Winchester? ### What is there to do in Winchester near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [3 Star Hotels in Old Town Winchester ](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - 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