Title: Upperville, VA Cottage Rentals from $221 | Expedia.com

[Upperville Travel Guide](https://expedia.com/Upperville.dx184116)[Hotels in Upperville](https://expedia.com/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Vacation Rentals in Upperville](https://expedia.com/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Flights to Upperville](https://expedia.com/Cheap-Flights-To-Upperville.d184116.Travel-Guide-Flights)[Car Rentals in Upperville](https://expedia.com/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.com/Upperville.d184116.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/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 three months

[May 29 - May 31](https://www.expedia.com/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)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-06-26&endDate=2026-06-28&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)

![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)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

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.

$359 nightly

$396 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.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)

![Living area](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/34c3bf25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Hamilton

[](https://www.expedia.com/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information)

9.8/10

Exceptional

(12 reviews)

"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jasmine M.

$344 nightly

$392 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.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)

![Property grounds](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4383aa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/ea22e17f.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)

### Cottage in Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information)

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.

$201 nightly

$221 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.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)

![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)

![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)

### Cottage in Leesburg's Old and Historic District

[](https://www.expedia.com/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.Hotel-Information)

9.8/10

Exceptional

(40 reviews)

"Great location, would stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eric D S.

$420 nightly

$483 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/0ee9ec99.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)

### Cottage in Middleburg

[](https://www.expedia.com/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information)

10/10

Exceptional

(57 reviews)

"Loved out stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emilee

$367 nightly

$394 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.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)

![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)

![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)

### Cottage in Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

10/10

Exceptional

(16 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.

$364 nightly

$401 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/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/73000000/72540000/72536300/72536217/dd999d68.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)

![Dining](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/5b5da494.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)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information)

9.8/10

Exceptional

(20 reviews)

"Great view, very secluded"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matt s.

$339 nightly

$377 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.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/f3f54889.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)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information)

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.

$323 nightly

$360 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.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)

![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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/197f6c5e.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)

### Cottage in Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information)

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.

$387 nightly

$430 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information)

10/10

Exceptional

(24 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.

$403 nightly

$449 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/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)

![Interior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/5b1052f3.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)

![Exterior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/ca2f5746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information)

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.

$332 nightly

$370 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information)

![](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/ca7572c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/23fa3709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/72dcbd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/w2560h1706x0y0-2b95dcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Paeonian Springs

[](https://www.expedia.com/Hamilton-Hotels-Cozy-Haven-Cottage-Wedding-And-Winery-Retreat-LeesburgPurcellville-Area.h126918397.Hotel-Information)

$404 nightly

$460 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-Cozy-Haven-Cottage-Wedding-And-Winery-Retreat-LeesburgPurcellville-Area.h126918397.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)

![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)

![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/90000000/89150000/89145600/89145580/31dbe26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information)

9.8/10

Exceptional

(25 reviews)

"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy P.

$301 nightly

$335 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/9341fc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.com/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information)

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.

$628 nightly

$699 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.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)

### Cottage in Leesburg

[](https://www.expedia.com/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information)

$1,603 nightly

$1,827 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information)

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## Top Upperville Hotel Reviews

![Home2 Suites by Hilton Leesburg](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603707/8a90ec52_y.jpg)

### Home2 Suites by Hilton Leesburg

10/10 Excellent

"The personnel is extremely helpful and polite. The cleanness and space of the room was great"

[](https://expedia.com/Leesburg-Hotels-Home2-Suites-By-Hilton-Leesburg.h90603707.Hotel-Information)

![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/bcd21d29_y.jpg)

### Best Western Leesburg Hotel & Conference Center

10/10 Excellent

"Staff was friendly to me and my kids"

[](https://expedia.com/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg)

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Nice facility, nice staff, and comfortable clean room. Superior exercise room. Suggest removing broken/non-functioning bottle fed water cooler in exercise room and having signage direct guests to water fountain “just around the corner by the elevator.“ Warm breakfast adequate and served in very comfortable, bright area. The only bill downside was fellow guests who were traveling with dogs. Despite the hotel, providing waste bags, prominently and posting signs asking guests to “pick up after your dog, please,” there was a grotesque amount of dog droppings all around the hotel exterior."

[](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/d75699e6_y.jpg)

### Holiday Inn Express Charles Town by IHG

10/10 Excellent

"Terrific room, exceptionally clean, good size, very nice staff, Good breakfast. Would highly recommend, even had free chocolate chip cookies in the lobby in the evenings. "

[](https://expedia.com/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.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

"Staff was great! Will go back"

[](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![18th Century Stone Cottage minutes from historic Middleburg](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/b94ceda5_y.jpg)

### 18th Century Stone Cottage minutes from historic Middleburg

10/10 Excellent

"Had an excellent time staying here, it was a blend if rustic and modern. Very cozy, and had everything you'd need for a truly relaxing stay. Tim made sure everything was on point for our time at the cottage. "

[](https://expedia.com/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Fantastic "

[](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information)

![The Inn at Charles Town - Hollywood Casino](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6291b142_y.jpg)

### The Inn at Charles Town - Hollywood Casino

10/10 Excellent

"Room was as expected. Very friendly staff, regardless of time of day."

[](https://expedia.com/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information)

![Clarion Hotel & Conference Center Leesburg](https://images.trvl-media.com/lodging/1000000/30000/24400/24372/cc06dfd9_y.jpg)

### Clarion Hotel & Conference Center Leesburg

10/10 Excellent

"Staff was nice. At the hotel… but… the lady that worked in the restaurant in the morning for breakfast was RUDE!! She followed myself and my fiancé as we made breakfast and didn’t follow any of the other guests (we are African American). She complained about us taking our breakfast to our room with the containers that the night guy GAVE TO US to take our dinner back to our room the night before! And then… she wrongly accused my fiancé of cursing at her the morning we checked out and followed us to the front desk and told the staff he cursed at her. We have stayed there before and Never had such an experience. "

[](https://expedia.com/Leesburg-Hotels-Clarion-Hotel-Conference-Center-Leesburg.h24372.Hotel-Information)

## Find out more about Upperville

## Upperville Cottages information

| Number of reviews | 294         |
| ----------------- | ----------- |
| Accommodation     | 90 Cottages |
| Lowest Price      | $221        |
| Highest Price     | $1,827      |

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