Title: Upperville, VA Cottage Rentals from $220 | 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 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-07-17&endDate=2026-07-19&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

![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)

### Royal Heritage Home @ Historic Leesburg

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

Leesburg's Old and Historic District

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.

$464 nightly

$534 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![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.com/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information)

Hamilton

9.8/10

Exceptional

(13 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 26 - Mar 27

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/52000000/51510000/51509100/51509047/9a866bf1.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)

### Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

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

$200 nightly

$220 total

Mar 30 - Mar 31

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)

![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)

![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 w/ Hot Tub and 100-Mile Valley Views!

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

$340 nightly

$378 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)

![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)

### Art Docko - Lakefront Artist Retreat w/ Hot Tub!

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

Harpers Ferry

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.

$401 nightly

$447 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/0ee9ec99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e29f28d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Middleburg

10/10

Exceptional

(57 reviews)

"Loved out stay! "

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

Emilee

$368 nightly

$395 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)

![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/5709e3b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/346044b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Peaceful Lakefront Cottage with Mountain Views!

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

Harpers Ferry

10/10

Exceptional

(33 reviews)

"The hot tub worked well. The place was clean. The location was fantastic. I had no problems but somebody may want to run the blower on wood burner and if I didn’t have 4 wheel drive; I would not get in and out of drive. For me the stay was fantastic "

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

Greg N.

$329 nightly

$366 total

Mar 26 - Mar 27

Total with taxes and fees

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

![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)

![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)

### Riverfront! Shenandoah River! Sleeps 4! New Hot Tub 

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

$389 nightly

$432 total

Mar 25 - Mar 26

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/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)

![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)

### Lake View Retreat - Cottage Near a Peaceful Lake!

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

$319 nightly

$355 total

Apr 9 - Apr 10

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/86000000/85480000/85477500/85477424/57edbddb.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/86000000/85480000/85477500/85477424/a2e5cceb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/80505805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/356b5bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

[](https://www.expedia.com/Boyce-Hotels-Pets-YES-Hot-Tub-Fire-Pit-Fast-Wi-Fi.h85477424.Hotel-Information)

Boyce

10/10

Exceptional

(32 reviews)

"Terrific host and property. Will definitely come back!"

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

Kevin P.

$614 nightly

$678 total

Apr 22 - Apr 23

Total with taxes and fees

[](https://www.expedia.com/Boyce-Hotels-Pets-YES-Hot-Tub-Fire-Pit-Fast-Wi-Fi.h85477424.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/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.com/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

Front Royal

10/10

Exceptional

(18 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.

$543 nightly

$599 total

Apr 13 - Apr 14

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)

![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)

![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/31dbe26c.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)

### Woodsy Retreat with a Hot Tub and Seasonal Views!

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

(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 31 - Apr 1

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)

![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) | 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/95000000/94960000/94956400/94956322/51da24ac.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)

### 'thomson Farm' Classic Home < 10 Mi to Vineyards!

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

Leesburg

$1,603 nightly

$1,827 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.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/110000000/109810000/109808300/109808234/76b41d19.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/e5ab5732.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.com/Leesburg-Hotels-Cottage-W-Furnished-Patio-Garden-Dtwn-Leesburg.h109808234.Hotel-Information)

Leesburg's Old and Historic District

$590 nightly

$679 total

Apr 23 - Apr 24

Total with taxes and fees

[](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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

"Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service."

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

"Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming."

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

![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg)

### Lansdowne Resort and Spa

10/10 Excellent

"Perfect"

[](https://expedia.com/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.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

8/10 Good

""Wheelchair accessible" room was that, but the bathroom lacked either a show chair or bench or, even more crucially, grab bars in the shower. Otherwise everything was 5 stars, but this really knocks it down a notch."

[](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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

"Room had some lamp bulb issues… the front desk didn’t get that info to maintenance but I ran into a maintenance man and he took care of it right away. Thank you! "

[](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

8/10 Good

"The room was very clean. The staff are friendly. Nice place to stay. "

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

![Hampton Inn by Hilton Gainesville-Haymarket](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/718360d7_y.jpg)

### Hampton Inn by Hilton Gainesville-Haymarket

8/10 Good

"The property was very clean, bathroom was amazing, and breakfast was good. It was close to everything we needed. The indoor pool was cold for my kids to swim and the ladder at the deeper end had very rough grip tape on steps which I totally understand but it scraped my grandaughters heel when she was climbing in.. Over all it was a very pleasant stay and we will use this hotel again. "

[](https://expedia.com/Gainesville-Hotels-Hampton-Inn-By-Hilton-Gainesville-Haymarket.h1828858.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

"Clean room"

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

![Clarion Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/df57d4c1_y.jpg)

### Clarion Inn Harpers Ferry - Charles Town

8/10 Good

"On first glance it seems like it is going to be old and in disrepair. It has been very well maintained and it was very clean. The bedding was impressive for the cost. I was pleasantly surprised. The breakfast was decent and better than a Marriott I stayed at the bought before. "

[](https://expedia.com/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information)

## Find out more about Upperville

## Upperville Cottages information

| Number of reviews | 315         |
| ----------------- | ----------- |
| Accommodation     | 86 Cottages |
| Lowest Price      | $220        |
| 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)