Title: Upperville Vacation Rentals from CA $324: Short-Term Rentals for 2026 | Expedia.ca

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![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

# Upperville Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-11&endDate=2026-01-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 12 - Jan 13](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-12&endDate=2026-01-13&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Upperville vacation rentals

![TV, fireplace](https://images.trvl-media.com/lodging/107000000/106280000/106275600/106275599/d28586ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/107000000/106280000/106275600/106275599/7eb5da2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106280000/106275600/106275599/86e9975f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/107000000/106280000/106275600/106275599/c7902a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aslan's How - Cabin with Valley Views & Hot Tub!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Aslans-How-Cabin-With-Valley-Views-And-Hot-Tub.h106275599.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(8 reviews)

"We stayed here for our honeymoon and it was very nice and peaceful "

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

Robert F.

CA $139

CA $525 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Aslans-How-Cabin-With-Valley-Views-And-Hot-Tub.h106275599.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/88de3563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/ca0816c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/50e7f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wild Hare Cottage

[](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information)

Purcellville

10/10

Exceptional

(10 reviews)

"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "

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

Jennifer K.

CA $175

CA $303 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/8234f630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/df219c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/4b3e4419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/e4b142a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Harpers-Ferry-Cabin-W-Hot-Tub.h92168268.Hotel-Information)

Harpers Ferry

9.2/10

Wonderful

(30 reviews)

"Gorgeous cabin, incredibly clean and well stocked with everything needed. Hot tub was amazing and clean and huge. Greatful for the hosts promptness in communication.Thank you!"

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

Samantha S.

CA $232

CA $415 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Harpers-Ferry-Cabin-W-Hot-Tub.h92168268.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107830000/107821800/107821741/5049d780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107830000/107821800/107821741/5dd5513a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107830000/107821800/107821741/c9ec1532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107830000/107821800/107821741/a7981933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Log Cabin w/ Hot Tub & Waterfront Patio!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lakefront-Log-Cabin-W-Dreamy-Waterfront-Patio.h107821741.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(14 reviews)

"Everything was great! We had a lovely stay."

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

Beth D.

CA $139

CA $489 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lakefront-Log-Cabin-W-Dreamy-Waterfront-Patio.h107821741.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/068d8c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/fa7cba31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/34c3bf25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

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

Hamilton

9.6/10

Exceptional

(10 reviews)

"It was a great place to starve whole experience was perfect. "

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

Jaime B.

CA $313

CA $546 total

includes taxes & fees

Jan 13 - Jan 14

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

![Dining](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/w1120h749x6y3-7738ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/ae64454b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/e896adbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/w1123h752x4y0-1474706a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Cozy-Getaway-With-Steam-Shower-Perfect-For-Couples-And-Families.h87800580.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(83 reviews)

"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"

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

Sara S.

CA $138

CA $381 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Cozy-Getaway-With-Steam-Shower-Perfect-For-Couples-And-Families.h87800580.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/8bcbc451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/f3f54889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/81983e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/be60aec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information)

Harpers Ferry

9.6/10

Exceptional

(21 reviews)

"The house was clean, had plenty of rooms and a fantastic location. "

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

Bryan N.

CA $139

CA $500 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/5b1052f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/ca2f5746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Peaceful Lakefront Cottage with Mountain Views!

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

Harpers Ferry

10/10

Exceptional

(31 reviews)

"Great location. Beautiful scenery. House was clean."

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

Brandon H.

CA $139

CA $506 total

includes taxes & fees

Jan 14 - Jan 15

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

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/e475b7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b94c46bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/55bd22b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Harpers Ferry

10/10

Exceptional

(23 reviews)

"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"

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

Matthew P.

CA $153

CA $624 total

includes taxes & fees

Jan 15 - Jan 16

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

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/e4739be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/ccd121a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/33aedc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury tiny home farm stay on historic property with hot tub in Stephens City

[](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

Stephens City

10/10

Exceptional

(1 review)

"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "

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

Chris F.

CA $182

CA $228 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/13365e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Bungalow in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

Front Royal

10/10

Exceptional

(12 reviews)

"Property was just what we were looking for "

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

Tim C.

CA $188

CA $308 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/0ea2fa7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/aa5ed80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/e0f90b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/85c7402b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Ridge Getaway - Sunset Views, A.T. Access

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Blue-Ridge-Getaway-Mountaintop-Cabin-With-Sunset-Views.h71514925.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(64 reviews)

"Comfortable, clean, welcoming, wonderful hot tub, great view from the porch!"

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

Carol M.

CA $139

CA $506 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Blue-Ridge-Getaway-Mountaintop-Cabin-With-Sunset-Views.h71514925.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/4072c02e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/f166d1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/74329033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/31dbe26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(24 reviews)

"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."

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

Claudia F.

CA $139

CA $472 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90701100/90701060/ea6a0436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90710000/90701100/90701060/926bba20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90710000/90701100/90701060/cc0cd162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90710000/90701100/90701060/b6d2985d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Wolf-Den-Airy-A-Frame-Cabin-With-Incredible-Valley-Views.h90701060.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(16 reviews)

"Great location. Great house. Could not have asked for more. "

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

A. Bland and D. T.

CA $139

CA $523 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Wolf-Den-Airy-A-Frame-Cabin-With-Incredible-Valley-Views.h90701060.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78300000/78294100/78294067/b2f46af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78300000/78294100/78294067/25129d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78300000/78294100/78294067/82ca2bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78300000/78294100/78294067/712c16bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Cabin a Stone's Throw From the A.T.!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Secluded-Mountain-Cabin-A-Stones-Throw-From-The-AT.h78294067.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(34 reviews)

"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "

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

Leonardf B.

CA $139

CA $523 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Secluded-Mountain-Cabin-A-Stones-Throw-From-The-AT.h78294067.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76330000/76328900/76328817/7ebfb5be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76330000/76328900/76328817/c9460acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, offices](https://images.trvl-media.com/lodging/77000000/76330000/76328900/76328817/8645d03a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, offices](https://images.trvl-media.com/lodging/77000000/76330000/76328900/76328817/73f65a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rebels Rest - Cabin with Enchanting Sunset Views!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Rebels-Rest-Mountaintop-Cabin-With-Enchanting-Sunset-Views.h76328817.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(31 reviews)

"Beautiful Sunsets, older cabin, not too steep of a drive up, outside deck is nice and fire pit area out front! Harper’s Ferry Area is cute and full of history! Be in shape to hike and climb while you are here, especially if you plan on doing a ghost walk after walking the town all day! 5 friends girls trip was great! "

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

Teresa R.

CA $139

CA $524 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Rebels-Rest-Mountaintop-Cabin-With-Enchanting-Sunset-Views.h76328817.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/dd999d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/c897e3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/113b4071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage w/ Hot Tub and 100-Mile Valley Views!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information)

Harpers Ferry

9.8/10

Exceptional

(20 reviews)

"Great view, very secluded"

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

Matt s.

CA $139

CA $524 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/94ade5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/4d2e26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/233346bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/7a807893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute cabin retreat near Shenandoah National Park and pet friendly!

[](https://www.expedia.ca/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

Linden

9.4/10

Exceptional

(13 reviews)

"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"

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

Bret L.

CA $170

CA $472 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/123000000/122700000/122691500/122691445/ba920c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122700000/122691500/122691445/7e021949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122700000/122691500/122691445/3e53c4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122700000/122691500/122691445/5a5e4b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing A-Frame Cabin in Harpers Ferry w/Sauna

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Relaxing-A-Frame-Cabin-In-Harpers-Ferry-WSauna.h122691445.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(2 reviews)

"Very clean, great amenities, comfortable!"

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

James

CA $223

CA $699 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Relaxing-A-Frame-Cabin-In-Harpers-Ferry-WSauna.h122691445.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/13764d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/4a787ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/fa4984f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/2e3f9865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Bluemont Village Home

[](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information)

Bluemont

10/10

Exceptional

(39 reviews)

"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"

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

Mary S.

CA $219

CA $596 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.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.ca/Hotel-Search?startDate=2026-01-25&endDate=2026-01-26&regionId=184116&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Upperville Hotel Reviews

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean room; really comfortable bed. Great staff "

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

"Basic accomodations but OK for the price. Everything worked fine andd hotel easy to get to from I-81\. "

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

"Loved the resort, the spa, everyone was so sweet. It was clean and smelled amazing. I had the absolute best massage ever. Love love love, me and my husband definitely will be back "

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

![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/d621c756_y.jpg)

### Best Western Leesburg Hotel & Conference Center

10/10 Excellent

"Breakfast was great, room was very clean, staff was super helpful and nice "

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

"Service was exceptional. It’s a small hotel, but was clean and great service. "

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

![Hampton Inn & Suites Charles Town](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed_y.jpg)

### Hampton Inn & Suites Charles Town

10/10 Excellent

"All the above They also had a shuttle to the casino"

[](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information)

![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg)

### Hampton Inn Winchester-University/Mall Area

10/10 Excellent

"Great breakfast. 24 hr coffee. Clean rooms. Pet friendly! Friendly front desk staff"

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

"Great staff"

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

![Clarion Hotel & Conference Center Leesburg](https://images.trvl-media.com/lodging/1000000/30000/24400/24372/8c4e2827_y.jpg)

### Clarion Hotel & Conference Center Leesburg

10/10 Excellent

"Clean and reasonable rate closer to my conferences."

[](https://expedia.ca/Leesburg-Hotels-Clarion-Hotel-Conference-Center-Leesburg.h24372.Hotel-Information)

## Find out more about Upperville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upperville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Upperville ](https://expedia.ca/Upperville-Private-Vacation-Homes.d184116-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Upperville ](https://expedia.ca/Upperville-Cabins.d184116-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Upperville ](https://expedia.ca/Upperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Upperville ](https://expedia.ca/Upperville-Apartments.d184116-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Upperville ](https://expedia.ca/Upperville-Agritourism.d184116-aaAgritourism.Travel-Guide-Accommodation)
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- [Guest Houses in Upperville ](https://expedia.ca/Upperville-Guest-Houses.d184116-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Upperville ](https://expedia.ca/Upperville-Chalets.d184116-aaChalets.Travel-Guide-Accommodation)
- [Villas in Upperville ](https://expedia.ca/Upperville-Villas.d184116-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Upperville ](https://expedia.ca/Upperville-Condos.d184116-aaCondos.Travel-Guide-Accommodation)
- [Lodges in Upperville ](https://expedia.ca/Upperville-Lodges.d184116-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Upperville ](https://expedia.ca/Upperville-Resort-Hotels.d184116-aaResortHotels.Travel-Guide-Accommodation)
- [RV Parks in Upperville ](https://expedia.ca/Upperville-RV-Parks.d184116-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Upperville ](https://expedia.ca/Upperville-Inns.d184116-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Upperville?

### What are some of the best vacation home rentals that Upperville has to offer?

### How many vacation rentals are there in Upperville?

### What can I see and do in Upperville?

### What are vacation rentals like in Upperville?

### Expedia's Latest Trends

Hotels

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Flights

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Activities

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Packages

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- [Virginia Beach Vacation Rentals](https://expedia.ca/Virginia-Beach-Vacation-Rentals.d10271.Travel-Guide-VacationRentals)

General

- [Visit Virginia Beach](https://expedia.ca/Virginia-Beach.dx10271)

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