Title: Upperville Cottages from CA $326 | Expedia.ca [Hotels in Upperville](https://expedia.ca/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Vacation Rentals in Upperville](https://expedia.ca/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Upperville Car Rentals](https://expedia.ca/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.ca/Upperville.d184116.Destination-Travel-Guides) ![Hiking Sky Meadows State Park...](https://images.trvl-media.com/place/553248621532661864/c5aca733-fee3-432b-92a4-5e362e7c66a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michael Gibson # Search Upperville Cottage Rentals from CA $326 - ![](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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=184116&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) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=184116&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) ## Our top choices for Upperville cottages ![Exterior](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/6364c41d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/4d2e2016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/f428f0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/c4395816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1800s Cozy Kitchen House in Berryville [](https://www.expedia.ca/Berryville-Hotels-1800s-Cozy-Kitchen-House-In-Berryville.h108361347.Hotel-Information) Berryville 10/10 Exceptional (1) "This unique gem was resurrected and rebirthed. It screams creativity and provides all of the comforts of home with the perfect balance between modern conveniences and days of yore. Great location for Harper’s Ferry goers. Definitely cannot say enough good things because it’s one helluva of a place to rest." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly G. CA $197 CA $253 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Berryville-Hotels-1800s-Cozy-Kitchen-House-In-Berryville.h108361347.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/5fb45cca.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/f3f54889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/7c522db1.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) ### 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 (21) "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 $137 CA $495 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/9cad6316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/19ec7694.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 (9) "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 $308 CA $536 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/4ee9e17b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/86ea8301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/3f2e7420.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) ### 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 (31) "Great location. Beautiful scenery. House was clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon H. CA $137 CA $498 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/4f1c9bf0.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) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b94c46bb.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) "My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew P. CA $150 CA $615 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0.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) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/1087f0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.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 9.8/10 Exceptional (10) "Love the view and beautiful appointed decor throughout the home…" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn M. CA $203 CA $500 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/50e7f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/789c6e52.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) ![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.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 (10) "Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer K. CA $191 CA $326 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/9a2bb6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/b8a5d193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/59a5c7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/4c56e3e1.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 (3) "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 $206 CA $563 total includes taxes & fees Jan 5 - Jan 6, 2026 [](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/73000000/72540000/72536300/72536217/7706e12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/91c01c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/3209a5cb.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) "Great view, very secluded" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt s. CA $159 CA $548 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/99ff3ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/13657af6.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/ad3ff238.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) "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 $137 CA $467 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/8c362a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/e639e91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/c9ca0b41.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 (7) "We enjoyed our stay , close to everything we planned for the weekend. Place was very roomy, clean and the beds were very comfortable!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl O. CA $217 CA $791 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/c8a1f4ff.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/cc14e518.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 (38) "The property was perfect for our stay. We had everything we needed and the beds were very comfy. We will definitely stay here again!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Andrew N. CA $293 CA $628 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.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/95000000/94960000/94956400/94956322/7e7ce3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/1732e5a3.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) ### '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 $1,485 CA $2,498 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.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/bc6898f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/5ce5fa13.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) "Loved out stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emilee CA $376 CA $538 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/a06f20db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/59b8161f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/47d3b88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/042e58ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi [](https://www.expedia.ca/Boyce-Hotels-NEW-WINE-COUNTRY-ESCAPE-Hot-Tub-Fire-Pit-Fast-Wi-Fi-Gas-Grill.h85477424.Hotel-Information) Boyce 10/10 Exceptional (32) "Good location. Large fenced in yard. Plenty of room. Would book again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Don M. CA $486 CA $987 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Boyce-Hotels-NEW-WINE-COUNTRY-ESCAPE-Hot-Tub-Fire-Pit-Fast-Wi-Fi-Gas-Grill.h85477424.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/d310e7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/5d5a16bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/6f7d1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/b2f47280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hike, Sip & Explore: Charming Waterford Cottage! [](https://www.expedia.ca/Waterford-Hotels-Hike.h116109067.Hotel-Information) Waterford CA $376 CA $662 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Waterford-Hotels-Hike.h116109067.Hotel-Information) ![Cottage (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808234/468c6ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808234/7b1b0532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808234/c51626d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808234/792fde61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage w/ Furnished Patio & Garden: Dtwn Leesburg [](https://www.expedia.ca/Leesburg-Hotels-Cottage-W-Furnished-Patio-Garden-Dtwn-Leesburg.h109808234.Hotel-Information) Leesburg's Old and Historic District CA $518 CA $928 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Leesburg-Hotels-Cottage-W-Furnished-Patio-Garden-Dtwn-Leesburg.h109808234.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=2026-01-10&endDate=2026-01-11®ionId=184116&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%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation) ## Top Upperville Hotel Reviews ![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 "My go to when visiting my parents. No frills, great price. Clean, decent coffee and breakfast (what you expect for the price) nice gym. Rooms are quiet. Bed comfortable and super easy parking. " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!" [](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 "The breakfast staff is helpful " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 "It would be nice if they had a business center that was actually a business center and not a storage room" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Clean and quiet" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Effortless check-in. Clean quiet room. Friendly staff" [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Great staff, clean room" [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/d621c756_y.jpg) ### Best Western Leesburg Hotel & Conference Center 10/10 Excellent "The room was clean for the most part. There was a little mold in the shower. The place was nice and quiet, and had a good breakfast for being free. Parking was nice and easy." [](https://expedia.ca/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ## Find out more about Upperville ## Upperville Cottages information | Number of reviews | 274 | | ----------------- | ----------- | | Accommodation | 90 Cottages | | Lowest Price | CA $326 | | Highest Price | CA $2,498 | ## Frequently asked questions ### Why book your cottage in Upperville with Expedia? ### How can I find cheap cottages in Upperville? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Ashville Hotels ](https://www.expedia.ca/Ashville-Hotels.d553248635975846883.Travel-Guide-Hotels) - [Luxury Hotels in Blue Ridge ](https://www.expedia.ca/Blue-Ridge-Hotels-Luxury-Hotel.0-0-d553248635976006713-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Blue Ridge ](https://www.expedia.ca/Blue-Ridge-Hotels-Marriott-Hotels-Resorts.0-0-d553248635976006713--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - 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