Title: Upperville, VA Cottage Rentals from $219 | 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)

![Welcome sign to Upperville Virginia in Fauquier County.](https://images.trvl-media.com/place/184116/deb8a32e-602b-43b9-802d-e775f9221444.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/184116/deb8a32e-602b-43b9-802d-e775f9221444.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg)  
###  
Bundle & Save  
Get more, spend less whenever you see Bundle & Save deals
- ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg)  
###  
OneKeyCash  
Earn OneKeyCash on all your eligible bookings
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg)  
###  
Upfront pricing  
We are not like the others - we include taxes and fees

## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.com/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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-07-10&endDate=2026-07-12&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/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)

### 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 20 - Mar 21

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)

![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/ea22e17f.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/52000000/51510000/51509100/51509047/3d60803b.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.

$199 nightly

$219 total

Mar 19 - Mar 20

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)

![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)

![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)

### 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.

$337 nightly

$375 total

Mar 26 - Mar 27

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)

![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)

![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/be60aec6.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)

### 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.

$321 nightly

$357 total

Mar 22 - Mar 23

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/55bd22b2.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.

$386 nightly

$431 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/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/f7d693d4.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)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.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

(17 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.

$388 nightly

$428 total

Mar 24 - Mar 25

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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/13f2f2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/b2928827.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/92000000/91040000/91035100/91035005/0bf6ace8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/c9ecf0f3.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.

$489 nightly

$562 total

Mar 19 - Mar 20

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)

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

### 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

$365 nightly

$392 total

Mar 30 - Mar 31

Total with taxes and fees

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

![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)

![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)

### 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.

$385 nightly

$428 total

Mar 19 - Mar 20

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/fd9e4075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Internet, bed sheets](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/w2559h1706x1y1-7e70ad4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/b164e2a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/494a4f70.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 23 - Mar 24

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)

![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)

### 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.

$302 nightly

$336 total

Mar 26 - Mar 27

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)

![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/b18e03f6.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)

![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

(33 reviews)

"Great location. Beautiful scenery. House was clean."

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

Brandon H.

$326 nightly

$363 total

Mar 24 - Mar 25

Total with taxes and fees

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

![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)

![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)

### 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.

$625 nightly

$696 total

Mar 19 - Mar 20

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/bee6d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/1bc8e0bd.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)

### 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 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.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.com/Hotel-Search?startDate=2026-04-01&endDate=2026-04-02&regionId=184116&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.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=APARTMENT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)[

Sign up, it's free

](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)

## Top Upperville Hotel Reviews

![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

6/10 Okay

"Yes"

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

"Location of hotel is great for walking to restaurants and shops. "

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

8/10 Good

"Good place to stay. "

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

![Salamander Resort And Spa](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/6dea7395_y.jpg)

### Salamander Resort And Spa

10/10 Excellent

"The spa treatments are amazing. In addition, the restaurant is excellent at making simple dish extra special. I highly recommend the avocado toast from the breakfast menu."

[](https://expedia.com/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.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 room, friendly staff "

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

![Home2 Suites by Hilton Charles Town](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/cbf060ec_y.jpg)

### Home2 Suites by Hilton Charles Town

10/10 Excellent

"Jaden was welcoming and professional"

[](https://expedia.com/Martinsburg-Hotels-Home2-Suites-By-Hilton-Charles-Town.h19217874.Hotel-Information)

![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/d7802d8b_y.jpg)

### Hilton Garden Inn Dulles North

8/10 Good

"Good goodbye "

[](https://expedia.com/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information)

![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg)

### Sleep Inn & Suites Winchester near University

10/10 Excellent

"Yes the kitchen was a blessing "

[](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information)

![Home2 Suites by Hilton Leesburg](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603707/ce474dae_y.jpg)

### Home2 Suites by Hilton Leesburg

10/10 Excellent

"Front desk ladies were very kind and helpful "

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

## Find out more about Upperville

## Upperville Cottages information

| Number of reviews | 291         |
| ----------------- | ----------- |
| Accommodation     | 90 Cottages |
| Lowest Price      | $219        |
| Highest Price     | $1,827      |

## 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
- Vacation Rentals
- Other

- [B&B in Paris ](https://www.expedia.com/Paris-Bed-And-Breakfast.d6050691-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Paris ](https://www.expedia.com/Paris-Cabins.d6050691-aaCabins.Travel-Guide-Accommodation)
- [Hotels near Paris Barns ](https://www.expedia.com/Paris-Barns-Hotels.0-l553248621532661865-0.Travel-Guide-Filter-Hotels)
- [Paris Hotels ](https://www.expedia.com/Paris-Hotels.d6050691.Travel-Guide-Hotels)
- [Luxury Hotels in Paris ](https://www.expedia.com/Paris-Hotels-Luxury-Hotel.0-0-d6050691-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Paris ](https://www.expedia.com/Paris-Hotels-Winery-Hotel.0-0-d6050691-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Paris ](https://www.expedia.com/Paris-Hotels-Hotels-With-Complimentary-Breakfast.0-0-d6050691-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels)
- [Hotel Wedding Venues Hotels in Paris ](https://www.expedia.com/Paris-Hotels-Wedding-Hotels.0-0-d6050691-tWeddingHotels.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Paris ](https://www.expedia.com/Paris-Hotels-Couples-Resorts-Hotels.0-0-d6050691-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Hotels near Sky Meadows State Park ](https://www.expedia.com/Sky-Meadows-State-Park-Hotels.0-l553248621532661864-0.Travel-Guide-Filter-Hotels)
- [Hotels near Delaplane Cellars ](https://www.expedia.com/Delaplane-Cellars-Hotels.0-l553248621532661863-0.Travel-Guide-Filter-Hotels)
- [Hotels near RdV Vineyards ](https://www.expedia.com/RdV-Vineyards-Hotels.0-l553248621532661862-0.Travel-Guide-Filter-Hotels)
- [Cottages in Rectortown ](https://www.expedia.com/Rectortown-Cottages.d3000355260-aaCottages.Travel-Guide-Accommodation)
- [Villas in Rectortown ](https://www.expedia.com/Rectortown-Villas.d3000355260-aaVillas.Travel-Guide-Accommodation)
- [Rectortown Hotels ](https://www.expedia.com/Rectortown-Hotels.d3000355260.Travel-Guide-Hotels)
- [B&B in Delaplane ](https://www.expedia.com/Delaplane-Bed-And-Breakfast.d3000355082-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Delaplane ](https://www.expedia.com/Delaplane-Cabins.d3000355082-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Delaplane ](https://www.expedia.com/Delaplane-Cottages.d3000355082-aaCottages.Travel-Guide-Accommodation)
- [Vacation Homes in Delaplane ](https://www.expedia.com/Delaplane-Private-Vacation-Homes.d3000355082-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Delaplane Hotels ](https://www.expedia.com/Delaplane-Hotels.d3000355082.Travel-Guide-Hotels)
- [Hilton Hotels in Delaplane ](https://www.expedia.com/Delaplane-Hotels-Hilton-Hotels.0-0-d3000355082--bHiltonHotels.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Delaplane ](https://www.expedia.com/4Star-Delaplane-Hotels.s40-0-d3000355082.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Delaplane ](https://www.expedia.com/5Star-Delaplane-Hotels.s50-0-d3000355082.Travel-Guide-Filter-Hotels)
- [Hotels near Glenwood Park ](https://www.expedia.com/Glenwood-Park-Hotels.0-l553248621532661869-0.Travel-Guide-Filter-Hotels)
- [Hotels near Aspen Dale Winery at the Barn ](https://www.expedia.com/Aspen-Dale-Winery-At-The-Barn-Hotels.0-l553248621532661858-0.Travel-Guide-Filter-Hotels)
- [Hotels near Barrel Oak Winery ](https://www.expedia.com/Barrel-Oak-Winery-Hotels.0-l553248621532661861-0.Travel-Guide-Filter-Hotels)
- [Hotels near Naked Mountain Winery & Vineyards ](https://www.expedia.com/Naked-Mountain-Winery-Vineyards-Hotels.0-l553248621532661859-0.Travel-Guide-Filter-Hotels)
- [Hotels near Bluemont Vineyard ](https://www.expedia.com/Bluemont-Vineyard-Hotels.0-l553248621587519004-0.Travel-Guide-Filter-Hotels)
- [Hotels near Watermelon Park Campground ](https://www.expedia.com/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels)
- [Resorts in Middleburg ](https://www.expedia.com/Middleburg-Resorts.d55837-aaResorts.Travel-Guide-Accommodation)
- [B&B in Middleburg ](https://www.expedia.com/Middleburg-Bed-And-Breakfast.d55837-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Middleburg ](https://www.expedia.com/Middleburg-Cabins.d55837-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Middleburg ](https://www.expedia.com/Middleburg-Cottages.d55837-aaCottages.Travel-Guide-Accommodation)
- [Vacation Homes in Middleburg ](https://www.expedia.com/Middleburg-Private-Vacation-Homes.d55837-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Guest Houses in Middleburg ](https://www.expedia.com/Middleburg-Guest-Houses.d55837-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Middleburg ](https://www.expedia.com/Middleburg-Motels.d55837-aaMotels.Travel-Guide-Accommodation)
- [Rv Parks in Middleburg ](https://www.expedia.com/Middleburg-RV-Parks.d55837-aaRVParks.Travel-Guide-Accommodation)
- [Condo Rentals in Middleburg ](https://www.expedia.com/Middleburg-Condos.d55837-aaCondos.Travel-Guide-Accommodation)
- [Middleburg Hotels ](https://www.expedia.com/Middleburg-Hotels.d55837.Travel-Guide-Hotels)
- [Hotels near The Boxwood Winery ](https://www.expedia.com/The-Boxwood-Winery-Hotels.0-l553248621532661867-0.Travel-Guide-Filter-Hotels)
- [Hotels near National Sporting Library & Museum ](https://www.expedia.com/National-Sporting-Library-Museum-Hotels.0-l553248621532661872-0.Travel-Guide-Filter-Hotels)
- [B&B in Bluemont ](https://www.expedia.com/Bluemont-Bed-And-Breakfast.d6348602-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Bluemont ](https://www.expedia.com/Bluemont-Cottages.d6348602-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Bluemont ](https://www.expedia.com/Bluemont-Cabins.d6348602-aaCabins.Travel-Guide-Accommodation)
- [Hotels near Tudor Day Spa ](https://www.expedia.com/Tudor-Day-Spa-Hotels.0-l553248621532661871-0.Travel-Guide-Filter-Hotels)
- [Resorts in Bluemont ](https://www.expedia.com/Bluemont-Resorts.d6348602-aaResorts.Travel-Guide-Accommodation)
- [Condo Rentals in Bluemont ](https://www.expedia.com/Bluemont-Condos.d6348602-aaCondos.Travel-Guide-Accommodation)
- [Farmstay in Bluemont ](https://www.expedia.com/Bluemont-Agritourism.d6348602-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Bluemont ](https://www.expedia.com/Bluemont-Villas.d6348602-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Bluemont ](https://www.expedia.com/Bluemont-Lodges.d6348602-aaLodges.Travel-Guide-Accommodation)
- [Motels in Bluemont ](https://www.expedia.com/Bluemont-Motels.d6348602-aaMotels.Travel-Guide-Accommodation)
- [Marriott Hotels & Resorts in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Marriott-Hotels-Resorts.0-0-d55837--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Hotels near The Byrne Gallery ](https://www.expedia.com/The-Byrne-Gallery-Hotels.0-l553248621532661875-0.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Winery-Hotel.0-0-d55837-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Pet-Friendly-Hotel.0-0-d55837-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Resorts & Hotels with Spas in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Spa-Hotel.0-0-d55837-tSpaHotel.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Middleburg ](https://www.expedia.com/4Star-Middleburg-Hotels.s40-0-d55837.Travel-Guide-Filter-Hotels)
- [Hotels with Restaurants in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Hotels-With-Restaurants.0-0-d55837-tHotelswithRestaurants.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Luxury-Hotel.0-0-d55837-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Hotel Wedding Venues Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Wedding-Hotels.0-0-d55837-tWeddingHotels.Travel-Guide-Filter-Hotels)
- [5 Star Hotels in Middleburg ](https://www.expedia.com/5Star-Middleburg-Hotels.s50-0-d55837.Travel-Guide-Filter-Hotels)
- [Gay friendly Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-LGBT-Welcoming-Hotel.0-0-d55837-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Romantic-Hotel.0-0-d55837-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Tennis Courts in Middleburg ](https://www.expedia.com/Middleburg-Hotels-Hotels-With-Tennis-Courts.0-0-d55837-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels)

- [Flights to Paris ](https://www.expedia.com/Cheap-Flights-To-Paris.d6050691.Travel-Guide-Flights)
- [Flights to Delaplane ](https://www.expedia.com/Cheap-Flights-To-Delaplane.d3000355082.Travel-Guide-Flights)
- [Flights to Middleburg ](https://www.expedia.com/Cheap-Flights-To-Middleburg.d55837.Travel-Guide-Flights)
- [Orlando to Middleburg ](https://www.expedia.com/lp/flights/178294/55837/orlando-to-middleburg)
- [Flights from Middleburg ](https://www.expedia.com/lp/flights/55837/flights-from-middleburg)

- [Paris Barns ](https://www.expedia.com/Paris-Barns-Paris.d553248621532661865.Vacation-Attraction)
- [Visit Paris ](https://www.expedia.com/Paris.dx6050691)
- [Sky Meadows State Park ](https://www.expedia.com/Sky-Meadows-State-Park-Virginia.d553248621532661864.Vacation-Attraction)
- [Delaplane Cellars ](https://www.expedia.com/Delaplane-Cellars-Delaplane.d553248621532661863.Vacation-Attraction)
- [Rdv Vineyards ](https://www.expedia.com/RdV-Vineyards-Delaplane.d553248621532661862.Vacation-Attraction)
- [Visit Rectortown ](https://www.expedia.com/Rectortown.dx3000355260)
- [Visit Delaplane ](https://www.expedia.com/Delaplane.dx3000355082)
- [Glenwood Park ](https://www.expedia.com/Glenwood-Park-Middleburg.d553248621532661869.Vacation-Attraction)
- [Aspen Dale Winery at the Barn ](https://www.expedia.com/Aspen-Dale-Winery-At-The-Barn-Delaplane.d553248621532661858.Vacation-Attraction)
- [Barrel Oak Winery ](https://www.expedia.com/Barrel-Oak-Winery-Marshall.d553248621532661861.Vacation-Attraction)
- [Naked Mountain Winery & Vineyards ](https://www.expedia.com/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction)
- [Bluemont Vineyard ](https://www.expedia.com/Bluemont-Vineyard-Bluemont.d553248621587519004.Vacation-Attraction)
- [Watermelon Park Campground ](https://www.expedia.com/Watermelon-Park-Campground-Berryville.d553248621532661928.Vacation-Attraction)
- [The Boxwood Winery ](https://www.expedia.com/The-Boxwood-Winery-The-Plains.d553248621532661867.Vacation-Attraction)
- [National Sporting Library & Museum ](https://www.expedia.com/National-Sporting-Library-Museum-Middleburg.d553248621532661872.Vacation-Attraction)
- [Tudor Day Spa ](https://www.expedia.com/Tudor-Day-Spa-Middleburg.d553248621532661871.Vacation-Attraction)
- [The Byrne Gallery ](https://www.expedia.com/The-Byrne-Gallery-Middleburg.d553248621532661875.Vacation-Attraction)
- [Visit Middleburg ](https://www.expedia.com/Middleburg.dx55837)
- [Red Fox Fine Art ](https://www.expedia.com/Red-Fox-Fine-Art-Middleburg.d553248621532661874.Vacation-Attraction)

- [Advantage Rent-A-Car Rental Cars in Paris ](https://www.expedia.com/Advantage-Rent-A-Car-Car-Rentals-In-Paris.d6050691-c3.Car-Rental-Guide-Suppliers)
- [Car rentals near Paris ](https://www.expedia.com/Car-Rentals-In-Paris.d6050691.Car-Rental-Guide)
- [Car rentals near Rectortown ](https://www.expedia.com/Car-Rentals-In-Rectortown.d3000355260.Car-Rental-Guide)
- [Car rentals near Bloomfield ](https://www.expedia.com/Car-Rentals-In-Bloomfield.d553248635975869306.Car-Rental-Guide)
- [Car rentals near Delaplane ](https://www.expedia.com/Car-Rentals-In-Delaplane.d3000355082.Car-Rental-Guide)
- [Car rentals near Zulla ](https://www.expedia.com/Car-Rentals-In-Zulla.d553248635975865924.Car-Rental-Guide)
- [Car rentals near Middleburg ](https://www.expedia.com/Car-Rentals-In-Middleburg.d55837.Car-Rental-Guide)
- [Hertz Rental Cars in Middleburg ](https://www.expedia.com/Hertz-Car-Rentals-In-Middleburg.d55837-c40.Car-Rental-Guide-Suppliers)

- [Paris Vacation Rentals ](https://www.expedia.com/Paris-Vacation-Rentals.d6050691.Travel-Guide-VacationRentals)
- [Delaplane Vacation Rentals ](https://www.expedia.com/Delaplane-Vacation-Rentals.d3000355082.Travel-Guide-VacationRentals)
- [Middleburg Vacation Rentals ](https://www.expedia.com/Middleburg-Vacation-Rentals.d55837.Travel-Guide-VacationRentals)

- [Things to do in Middleburg ](https://www.expedia.com/Things-To-Do-In-Middleburg.d55837.Travel-Guide-Activities)