Title: Upperville Apartment Rentals from CA $198 | Expedia.ca

[Hotels in Upperville](https://expedia.ca/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Vacation Rentals in Upperville](https://expedia.ca/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Upperville Car Rentals](https://expedia.ca/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.ca/Upperville.d184116.Destination-Travel-Guides)

![Hiking Sky Meadows State Park...](https://images.trvl-media.com/place/553248621532661864/008a9705-5d69-4bff-87e9-dd23f82e56ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Michael Gibson

# Search Apartment Rentals in Upperville

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## Check prices for these dates

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-02-06&endDate=2026-02-08&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

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1118h1128x0y0-c29ed3e7.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)

![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/w1136h1516x18y15-0867a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester Historic District

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

8.0/10

Very good

(2)

"Small but appropriately priced."

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

John M.

CA $152

CA $267 total

includes taxes & fees

Dec 11 - Dec 12

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

![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)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/4e3d8e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Apartment in Bluemont

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

8.8/10

Excellent

(6)

"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.

CA $187

CA $374 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.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/89000000/88210000/88205300/88205213/8bb88bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/ff062017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/16ee56a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Warrenton

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

9.8/10

Exceptional

(59)

"Bill’s place was great. Everything was just as described, clean, and comfortable. Bill was very kind and helpful! Awesome stay!"

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

Joanne R.

CA $211

CA $324 total

includes taxes & fees

Dec 11 - Dec 12

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

![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)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w507h683x259y0-313a4f70.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.ca/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

CA $85

CA $198 total

includes taxes & fees

Dec 21 - Dec 22

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

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/56f94878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/7c5314f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/19fffcf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/4793a0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fauquier County

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

8.0/10

Very good

(1)

"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.

CA $180

CA $440 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Living area](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1117h810x5y0-b88c2c12.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)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1248h1670x0y0-152d5b6b.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/108000000/107900000/107895800/107895789/0da8d534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

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

10/10

Exceptional

(2)

"Great property with all the comforts of home"

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

Kristen R.

CA $246

CA $449 total

includes taxes & fees

Dec 11 - Dec 12

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

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w904h683x60y0-64dd4a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w905h683x60y0-d85c4b2b.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)

![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.ca/Middleburg-Hotels-Cosy-Studio-On-An-Organic-Farm.h95042415.Hotel-Information)

9.8/10

Exceptional

(22)

"The studio was good for the two of us and our dogs. It is very clean and comfortable s on a farm which we found appealing. Very convenient to restaurants (Middleburg) though a distance from dog-friendly wineries. I would definitely recommend it for a short stay. "

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

Jill P.

CA $208

CA $374 total

includes taxes & fees

Dec 14 - Dec 15

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

![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/ecd62a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/10ab8517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/73607a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/a0dcd3d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Gainesville

[](https://www.expedia.ca/Gainesville-Hotels-Balcony-Pool-Access-Modern-Gainesville-Home.h112522717.Hotel-Information)

CA $219

CA $689 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Gainesville-Hotels-Balcony-Pool-Access-Modern-Gainesville-Home.h112522717.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/10901b08.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)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/1592611e.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.ca/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information)

10/10

Exceptional

(21)

"Great place to stayed "

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

Mike F.

CA $187

CA $322 total

includes taxes & fees

Dec 11 - Dec 12

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

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/fb88912d.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)

![Interior](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/c4d6d514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Warrenton

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

10/10

Exceptional

(4)

"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.

CA $228

CA $368 total

includes taxes & fees

Dec 17 - Dec 18

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

![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)

![Living area](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/5028cd1c.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)

### Apartment in Bluemont

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

10/10

Exceptional

(3)

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

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

Daniel D.

CA $168

CA $350 total

includes taxes & fees

Dec 12 - Dec 13

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/6413f00b.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/56b2f1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/320dbc4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Amissville

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

9.6/10

Exceptional

(37)

"My wife and I enjoyed our stay at this cute and cozy spot. Very convenient for exploring Northern Virginia, from Shenandoah National Park, to Leesburg, Culpeper, Manassas, and beyond. Check-in was very easy and Jimmie, our host, was very friendly and responsive. "

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

John P.

CA $168

CA $323 total

includes taxes & fees

Dec 11 - Dec 12

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

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/434367ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/ace40b05.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)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/4cf065b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

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

9.0/10

Wonderful

(14)

"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.

CA $256

CA $460 total

includes taxes & fees

Dec 11 - Dec 12

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/01fca712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/dce8d0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Apartment in Winchester Historic District

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

8.6/10

Excellent

(4)

"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."

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

matthew r.

CA $191

CA $323 total

includes taxes & fees

Dec 16 - Dec 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/765a953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/fe22c400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/85465173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/f2a89cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

[](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information)

7.6/10

Good

(4)

"We loved the character and personality kf both Winchester and"

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

Jenna N.

CA $202

CA $356 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/0f5f7b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/36f6e97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/a05887b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/642d5e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Delaplane

[](https://www.expedia.ca/Farm-Suite-At-Valley-View-Farm.h121935788.Hotel-Information)

CA $242

CA $467 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Farm-Suite-At-Valley-View-Farm.h121935788.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)

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

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/cf8e60e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/31a46244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

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

9.0/10

Wonderful

(6)

"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.

CA $284

CA $513 total

includes taxes & fees

Dec 11 - Dec 12

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

![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)

![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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/5e1231b8.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.ca/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information)

6.0/10

(1)

CA $152

CA $275 total

includes taxes & fees

Dec 18 - Dec 19

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

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.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/b3502d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/facc3b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

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

9.6/10

Exceptional

(5)

"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "

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

Stephanie L.

CA $307

CA $548 total

includes taxes & fees

Dec 29 - Dec 30

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bb213bf2.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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/23f512b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/685d4771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Town Winchester

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

CA $305

CA $540 total

includes taxes & fees

Dec 15 - Dec 16

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

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Villas

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Private vacation homes

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=HOUSE_BOAT)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CHALET)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=RESIDENCE)

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## Top Upperville Hotel Reviews

![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg)

### Holiday Inn Express Charles Town by IHG

10/10 Excellent

"Everything was great"

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

![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg)

### Travelodge by Wyndham Winchester

10/10 Excellent

"Room clean, heater works great parking "

[](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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

"Front desk staff was sweet. Checking out was a breeze. Room was great. Great Oishi restaurant, basically in the parking lot ! Would definitely stay here again "

[](https://expedia.ca/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

"Staff is fantastic and breakfast is always great. "

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

![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg)

### Comfort Inn & Suites Winchester

10/10 Excellent

"Nice facility right off the highway. Clean, comfortable and large room. Staff were very nice. Easy parking. Next door to movies. "

[](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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

"Wonderful Thanksgiving weekend! Loved your resort "

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

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg)

### SpringHill Suites by Marriott Winchester

10/10 Excellent

"Clean room, courteous and professional staff. Great breakfast selections"

[](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg)

### Hampton Inn Front Royal

10/10 Excellent

"Everything was great about this Hampton Inn. It's dog friendly so i didn't know what to expect. It was very clean, nicely decorated (not dated) and the staff was super nice. Highly recommend it."

[](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Great hotel and staff"

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

## Find out more about Upperville

## Upperville Apartments information

| Number of reviews | 179           |
| ----------------- | ------------- |
| Accommodation     | 70 Apartments |
| Lowest Price      | CA $198       |
| Highest Price     | CA $689       |

## Frequently asked questions

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

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