Title: Best Cottages in Upperville in 2026 | Expedia.co.uk [Hotels in Upperville](https://expedia.co.uk/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Holiday Rentals in Upperville](https://expedia.co.uk/Upperville-Holiday-Rentals.d184116.Travel-Guide-HolidayRentals)[Upperville Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Upperville.d184116.Car-Hire-Guide)[Upperville Holidays](https://expedia.co.uk/Upperville.d184116.Holidays-City-Breaks) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [20 Feb - 22 Feb](https://www.expedia.co.uk/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) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=184116&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 [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=184116&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 [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=184116&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 Upperville 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) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/212d2c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/0c0a82ed.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.co.uk/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. £270 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain Top hot tub overlooking the Shenandoah River [](https://www.expedia.co.uk/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) Front Royal 10/10 Exceptional (15 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. £289 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.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) ![Interior](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/55bd22b2.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) ![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.co.uk/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. £323 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.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) ![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) ![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/f3f54889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake View Retreat - Cottage Near a Peaceful Lake! [](https://www.expedia.co.uk/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. £264 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.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/bee6d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/06cf4e8d.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.co.uk/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information) Leesburg £1,342 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.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) ![Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/88de3563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wild Hare Cottage [](https://www.expedia.co.uk/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 £164 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4a296327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/3d60803b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/9a866bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4383aa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View [](https://www.expedia.co.uk/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information) Front Royal 9.6/10 Exceptional (17 reviews) "Nice place, comfortable bed. Close to hiking in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake M. £180 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/d6f1c9e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/9341fc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs [](https://www.expedia.co.uk/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. £389 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.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) ![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.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) ![Exterior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/c897e3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage w/ Hot Tub and 100-Mile Valley Views! [](https://www.expedia.co.uk/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. £280 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.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) ![Exterior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/ca2f5746.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) ![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.co.uk/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. £272 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.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) ![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/31dbe26c.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) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/56bd2995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodsy Retreat with a Hot Tub and Seasonal Views! [](https://www.expedia.co.uk/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. £249 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/682637e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/34c3bf25.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) ### The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country! [](https://www.expedia.co.uk/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. £287 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/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) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/05617209.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) ### Royal Heritage Home @ Historic Leesburg [](https://www.expedia.co.uk/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. £344 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/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) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e29f28d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/2b9acd11.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.co.uk/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 £288 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/63526894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/2f7695a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/6d4d454a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/ea22ac13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront! Shenandoah River! Sleeps 4! New Hot Tub [](https://www.expedia.co.uk/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information) Front Royal 9.8/10 Exceptional (14 reviews) "Excellent place to stay. Shelly is an excellent host. Nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa H. £349 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.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.co.uk/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=184116&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CABIN) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VILLA) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation) ## Top Upperville Hotel Reviews ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Room was great and breakfast was ok but had waffles" [](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn & Suites Charles Town](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed_y.jpg) ### Hampton Inn & Suites Charles Town 10/10 Excellent "The staff was amazing at check in and out. The room was spotless and the pool was top notch. We will definitely stay here on our next trip to Charlestown " [](https://expedia.co.uk/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.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 "The room was spotless , and the staff was very curtis" [](https://expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 "Room type: Two double beds second floor Very clean, pretty spacious overall Cold refrigerator unlike some hotels’ refrigerators which are not cold enough Appreciated the armchair plus good-sized desk and chair large mirror by the door bathroom wall-to-wall counter space Friendly staff (very important) Beautiful baby grand piano in the lobby Surprised by the good hot breakfast - in a spacious well-ventilated area, better than I expected at this nightly fee CVS 4 minute walk Although the hotel could use some updating, the main things were great: safe, very clean bedding and towels, convenient location, ample parking, welcoming staff In my opinion this hotel is the best choice for its fee range. I do not want to spend an arm and a leg for a safe, clean place overnight and I don’t want an unsafe or unclean place for a cheap fee either. " [](https://expedia.co.uk/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg) ### Holiday Inn Express Charles Town by IHG 10/10 Excellent "Everything was excellent! Very impressed with this hotel from the staff, to cleanliness, to the rooms, to the breakfast buffet. Also the location and proximity to the casino is perfect!" [](https://expedia.co.uk/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg) ### Hilton Garden Inn Dulles North 10/10 Excellent "Clean room,.nice staff, large walk-in shower, coffee maker and mini fridge! Great price, saved 20 bucks online with Expedia app! I will definitely come back for another "staycation" " [](https://expedia.co.uk/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.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.co.uk/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.co.uk/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg) ### Hampton Inn Winchester N/Conference Center, VA 10/10 Excellent "The staff was wonderful! " [](https://expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ## Find out more about Upperville ## Upperville Cottages information | Number of reviews | 275 | | ----------------- | ----------- | | Accommodation | 90 Cottages | | Lowest Price | £164 | | Highest Price | £1,342 | ## 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 - More ways to book - [Book Cottages in Upperville on Expedia.com ](https://www.expedia.com/Upperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)