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)

![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

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-07-03&endDate=2026-07-05&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/d5eb0f37.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.

$366 nightly

$404 total

Mar 15 - Mar 16

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)

![Exterior](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4a296327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/3d60803b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 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 10 - Mar 11

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)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 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.

$380 nightly

$420 total

Mar 15 - Mar 16

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)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/8d8c27be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/682637e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/068d8c39.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)

### 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 11 - Mar 12

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.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.

$335 nightly

$373 total

Mar 19 - Mar 20

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)

![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/988526b2.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)

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

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/1cadeb55.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.

$432 nightly

$497 total

Mar 10 - Mar 11

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)

![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)

### 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 10 - Mar 11

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)

![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)

![Dining](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/2f7695a1.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)

### 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 10 - Mar 11

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/76000000/75200000/75194000/75193967/44a70f96.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)

![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)

### 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.

$327 nightly

$364 total

Mar 11 - Mar 12

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)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.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)

### 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.

$408 nightly

$454 total

Mar 12 - Mar 13

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/90000000/89150000/89145600/89145580/f515f3a1.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/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.

$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)

![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)

### 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.

$335 nightly

$373 total

Mar 12 - Mar 13

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/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/127000000/126920000/126918400/126918397/494a4f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/127000000/126920000/126918400/126918397/w2559h1707x0y0-8c953355.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 15 - Mar 16

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/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)

![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)

![Dining](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/76e1ebf5.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.

$633 nightly

$704 total

Mar 10 - Mar 11

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/95000000/94960000/94956400/94956322/51da24ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 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 10 - Mar 11

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=2026-03-23&endDate=2026-03-24&regionId=184116&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_184116)

## 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=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CABIN)

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=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&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=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&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=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&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=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&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

![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

"The hotel was conveniently located in town, even for a guest without a car on hand! Staff was AMAZING! Breakfast was solid and on time! Clean rooms and easy to navigate. "

[](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

"No complaints. The staff was amazing. Room was nice. The breakfast was good. "

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

"I have stayed at Landsdowne many years, typically for girls spa weekends or overnight stay while I’m in town. The Spa Experience is always phenomenal. The staff is friendly all around. I continue to enjoy my stays!"

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

10/10 Excellent

"Nice pool"

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

![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg)

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean rooms."

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

"very nice hotel,very clean"

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

![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/e7acb022_y.jpg)

### Hilton Garden Inn Dulles North

2/10 Terrible

"The TV didn’t work. "

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

6/10 Okay

"Safe but no hot water. "

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

2/10 Terrible

"This Sleep Inn is not clean or well maintained. A sofa in our room, 318, was stained, torn upholstery and dirty.. The parking lot was dark at night, with sparse and broken lights. The ice machine was dirty with no ice available. The elevator had no inspection certificate.. Expedia should not include this location in searches."

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

## Find out more about Upperville

## Upperville Cottages information

| Number of reviews | 295         |
| ----------------- | ----------- |
| Accommodation     | 90 Cottages |
| Lowest Price      | $221        |
| 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)