Title: Best Apartments in Upperville, VA for Your Vacation from $176 | 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)

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## 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 apartments

![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/9afb48f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/e90c6032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/b988c9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/649fbfb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bluemont

[](https://www.expedia.com/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

8.8/10

Excellent

(6 reviews)

"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "

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

Haley M.

$239 nightly

$272 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/c7a94a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/1b928033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/902ff11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

9.0/10

Wonderful

(15 reviews)

"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."

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

Tracy F.

$288 nightly

$326 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/d8cde914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/40b498de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/9a8809aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/w2094h1573x3y0-24e0533e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bluemont

[](https://www.expedia.com/Bluemont-Hotels-Stylish-1-Bd1-Ba-Gardern-Apt-Within-Quaint-Bluemont-Village.h118716576.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Had a fun visit. Property and host we're excellent."

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

Daniel D.

$243 nightly

$277 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Bluemont-Hotels-Stylish-1-Bd1-Ba-Gardern-Apt-Within-Quaint-Bluemont-Village.h118716576.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/ba92ae27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/9de8a9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/ca492496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/4f7ea815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Linden

[](https://www.expedia.com/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information)

10/10

Exceptional

(22 reviews)

"Great place to stayed "

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

Mike F.

$205 nightly

$226 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125790000/125780900/125780824/8cc1019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125790000/125780900/125780824/14bf6fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/126000000/125790000/125780900/125780824/26023006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125790000/125780900/125780824/4860b9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Purcellville

[](https://www.expedia.com/Purcellville-Hotels-Cozy-Apartment-W-King-Bed-In-Lovely-VA-Wine-Country-Enough-Room-For-Up-To-6.h125780824.Hotel-Information)

10/10

Exceptional

(1 review)

"Had a wonderful stay. The space was very cute and was clean and comfortable. The hosts were helpful and accommodating. We appreciated everything. "

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

Amanda H.

$179 nightly

$200 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Purcellville-Hotels-Cozy-Apartment-W-King-Bed-In-Lovely-VA-Wine-Country-Enough-Room-For-Up-To-6.h125780824.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66730000/66720800/66720787/e3a60a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66730000/66720800/66720787/7bcf1f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66730000/66720800/66720787/fc3ca014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66730000/66720800/66720787/6a99d517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in The Plains

[](https://www.expedia.com/Marshall-Hotels-Alpaca-Farm-Studio-Apartment.h66720787.Hotel-Information)

9.8/10

Exceptional

(9 reviews)

"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."

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

Joe D.

$474 nightly

$509 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Marshall-Hotels-Alpaca-Farm-Studio-Apartment.h66720787.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1129h837x5y0-f4d1c4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/1b3ed1b6_edited_3046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/7def9f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/288bbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-Morocco-Loft-2BR-Overlooking-City-Walking-Mall.h107895789.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Great property with all the comforts of home"

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

Kristen R.

$286 nightly

$324 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Morocco-Loft-2BR-Overlooking-City-Walking-Mall.h107895789.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/a2cdbfd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/c8d5bd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/8bb88bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, electric kettle, toaster](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/c12bdaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Warrenton

[](https://www.expedia.com/Warrenton-Hotels-Historic-Apartment-In-Old-Town-Warrenton.h88205213.Hotel-Information)

9.8/10

Exceptional

(61 reviews)

"The apartment was extremely nice. Everything that was needed for a great stay. I would definitely stay there again."

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

Tommy N.

$207 nightly

$226 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Warrenton-Hotels-Historic-Apartment-In-Old-Town-Warrenton.h88205213.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/da01b17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/90d79bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/d2b308f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/b89de05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Amissville

[](https://www.expedia.com/Amissville-Hotels-Cozy-1BR-Apt-Minutes-From-Skyline-Drive.h88519350.Hotel-Information)

9.8/10

Exceptional

(42 reviews)

"Cozy and clean. We enjoy the peace and quiet and a great and safe area and neighborhood. "

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

Theresa S.

$217 nightly

$228 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Amissville-Hotels-Cozy-1BR-Apt-Minutes-From-Skyline-Drive.h88519350.Hotel-Information)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w507h683x258y0-1b65640c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w507h683x259y0-e00c7c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w301h683x362y0-6f04a930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w424h683x300y0-9f1b99bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Middleburg

[](https://www.expedia.com/Middleburg-Hotels-Cosy-Studio-On-An-Organic-Farm.h95042415.Hotel-Information)

9.8/10

Exceptional

(24 reviews)

"We had an excellent time and our dog loved the farm. The hosts are fantastic people and were very helpful. The room was clean and comfortable. We location is nice just a few minutes drive from downtown Middleburg and in a beautiful area. We will definitely return."

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

Henri G.

$233 nightly

$266 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Middleburg-Hotels-Cosy-Studio-On-An-Organic-Farm.h95042415.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/48866a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/67cf4cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/fe01edb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/3b8786c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Warrenton

[](https://www.expedia.com/Warrenton-Hotels-Charming-1-Bedroom-Apartment-In-Old-Town-Warrenton.h118097810.Hotel-Information)

10/10

Exceptional

(5 reviews)

"I love staying here! It's cozy and comfortable and in a perfect location. "

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

Jenny D.

$243 nightly

$266 total

Mar 21 - Mar 22

Total with taxes and fees

[](https://www.expedia.com/Warrenton-Hotels-Charming-1-Bedroom-Apartment-In-Old-Town-Warrenton.h118097810.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/4d85dcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/4a8d2d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/0531b121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/6944d33b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-Pretty-Little-Apt-By-The-Train-II.h75853307.Hotel-Information)

9.8/10

Exceptional

(7 reviews)

"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."

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

Stephanie L.

$190 nightly

$215 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Pretty-Little-Apt-By-The-Train-II.h75853307.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1136h1516x18y15-0867a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/a601c23d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1133h1513x0y23-fd248447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1118h1128x0y0-c29ed3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester Historic District

[](https://www.expedia.com/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information)

8.0/10

Very Good

(2 reviews)

"Small but appropriately priced."

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

John M.

$170 nightly

$193 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/5c313978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/24f9c33c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/8a7ae46b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/07dac09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fauquier County

[](https://www.expedia.com/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information)

8.0/10

Very Good

(1 review)

"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...

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

Kathy S.

$285 nightly

$288 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/w1080h1606x0y6-7da3475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/58d1022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/43e19b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/9ba529c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester Historic District

[](https://www.expedia.com/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information)

6.0/10

(1 review)

$175 nightly

$198 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x260y0-1afec896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/3aaa43b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x259y0-d4dd74ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/ff2d50c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester

[](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

$162 nightly

$176 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e0ae9bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e55c3864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/aac25142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/4ef124d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information)

9.8/10

Exceptional

(6 reviews)

"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "

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

Larry E.

$346 nightly

$392 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/80b59f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1413h1055x0y0-6561893b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1267h918x0y5-1650c869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information)

9.0/10

Wonderful

(6 reviews)

"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"

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

Tricia M.

$318 nightly

$360 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/9e880709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/1f4dbb15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/e0865dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bd1270e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.com/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Beautiful space; helpful host."

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

Sally C.

$344 nightly

$390 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b26f42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b64b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2ce760e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2f99002c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester Historic District

[](https://www.expedia.com/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information)

8.6/10

Excellent

(4 reviews)

"Large historic house at a great location "

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

Bryan T.

$203 nightly

$230 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.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=2026-03-29&endDate=2026-03-30&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)

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## 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=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&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=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&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=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&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=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&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=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=CHALET)

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## Top Upperville Hotel Reviews

![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

"We always enjoy our stay here. The front desk staff is always amazing! Very nice, friendly and welcoming. "

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

"Clean room"

[](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄"

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

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

### Best Western Leesburg Hotel & Conference Center

10/10 Excellent

"The staff is excellent"

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

![Holiday Inn Express & Suites Leesburg - Historic District by IHG](https://images.trvl-media.com/lodging/1000000/600000/596500/596430/c6a38a54_y.jpg)

### Holiday Inn Express & Suites Leesburg - Historic District by IHG

8/10 Good

"Room was clean and matched the photos online. The breakfast offered met my needs."

[](https://expedia.com/Leesburg-Hotels-Holiday-Inn-Express-And-Suites-Leesburg-Historic-District.h596430.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

"Clean, heater a little noisy"

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

![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/c10d527c_y.jpg)

### Hampton Inn Winchester-University/Mall Area

10/10 Excellent

"Everything was very lovely and cozy and the AC worked perfectly "

[](https://expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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

"Cute location "

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

"Our stay was wonderful. The room was great and the staff were very polite and helpful"

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

## Find out more about Upperville

## Upperville Apartments information

| Number of reviews | 210           |
| ----------------- | ------------- |
| Accommodation     | 70 Apartments |
| Lowest Price      | $176          |
| Highest Price     | $509          |

## Frequently asked questions

### What's it like to stay at an apartment in Upperville?

### How do you know if an apartment is the best choice for you?

### What's the top apartment for a stay in Upperville?

### What can I expect from the weather in Upperville?

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### What's the best way to get to and around Upperville?

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