Title: Best Apartments in Upperville, VA for Your Vacation from $164 | 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

[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 apartments

![Smart TV](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/da01b17c.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/221408fe.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)

"Love that my pet was welcome. Very quiet location and felt like home. "

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

Theresa S.

$217 nightly

$228 total

Mar 24 - Mar 25

Total with taxes and fees

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

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

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/b7a39e49.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.

$206 nightly

$227 total

Mar 24 - Mar 25

Total with taxes and fees

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66730000/66720800/66720787/f0c5955a.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.

$472 nightly

$506 total

Mar 24 - Mar 25

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)

![Dining](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1025h1046x4y3-ad71c285.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/108000000/107900000/107895800/107895789/1b3ed1b6_edited_3046.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.

$284 nightly

$322 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/a47a043f.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.

$233 nightly

$266 total

Mar 24 - Mar 25

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/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)

![Microwave, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/3e63ad06.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.

$236 nightly

$269 total

Mar 24 - Mar 25

Total with taxes and fees

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

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

![Interior](https://images.trvl-media.com/lodging/126000000/125790000/125780900/125780824/86ee8df6.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

(2 reviews)

"Great place to stay while in Purcellville! Super close to everything in town. Clean and smelled great. Easy check in process and the owners are very responsive. Thanks!"

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

Brian L.

$179 nightly

$200 total

Mar 26 - Mar 27

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)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/c7a94a89.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.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)

### 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.

$292 nightly

$331 total

Mar 24 - Mar 25

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w905h683x59y0-b8703cd0.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.

$232 nightly

$264 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)

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/8bb88bf4.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 30 - Mar 31

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/c4d6d514.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)

![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.

$246 nightly

$269 total

Mar 30 - Mar 31

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/121000000/120420000/120414100/120414068/5c313978.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/f803f4c1.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)

![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)

### 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.

$283 nightly

$285 total

Mar 24 - Mar 25

Total with taxes and fees

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

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

![TV](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/70052fb7.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)

### 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)

![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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/d01496c8.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)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/58d1022d.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/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/w1129h841x0y0-0b4a0cfb.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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.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)

### 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.

$345 nightly

$391 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.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/w507h683x259y0-313a4f70.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)

![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)

$151 nightly

$164 total

Apr 19 - Apr 20

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1267h918x0y5-1650c869.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)

![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.

$326 nightly

$369 total

Mar 24 - Mar 25

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)

![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/120000000/119110000/119109900/119109888/1f4dbb15.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.

$343 nightly

$389 total

Mar 24 - Mar 25

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)

![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)

![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)

![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=2026-04-06&endDate=2026-04-07&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

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Private vacation homes

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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)

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## 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

"Everything was great. Loved how fluffy the pillows were "

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

![Courtyard by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b_y.jpg)

### Courtyard by Marriott Winchester

10/10 Excellent

"Staff is friendly and the rooms are clean. Location is convenient to everything in Winchester "

[](https://expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.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)

![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

"Great"

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

![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

"Nice place"

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

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

### Salamander Resort And Spa

10/10 Excellent

"Best stat ever! We love love love the Salamander!"

[](https://expedia.com/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information)

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

### Lansdowne Resort and Spa

8/10 Good

"Beautiful hotel -rooms were very spacious, pool was great, bar has nice selection and staff. We were there in March so outdoor pool etc was not open but it looked pretty with waterfalls etc.Spa was nice but very expensive. "

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

## Find out more about Upperville

## Upperville Apartments information

| Number of reviews | 157           |
| ----------------- | ------------- |
| Accommodation     | 70 Apartments |
| Lowest Price      | $164          |
| Highest Price     | $506          |

## 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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