Title: Upperville Vacation Home Rentals from CA $301: Search Top Private Vacation Homes for Rent | 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)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-06-26&endDate=2026-06-28&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 homes

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

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/c5c32d53.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)

![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)

### Vacation Home in Front Royal

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

10/10

Exceptional

(14 reviews)

"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"

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

Brian B.

CA $184

CA $301 total

includes taxes & fees

Mar 3 - Mar 4

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/a3bac066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/54813276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/b5734027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/a9faaa4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Dog-Friendly-Cottage-W-Playground.h106325979.Hotel-Information)

9.6/10

Exceptional

(16 reviews)

"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "

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

Corrin D.

CA $219

CA $398 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Middletown-Hotels-Dog-Friendly-Cottage-W-Playground.h106325979.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/5441842b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/e073d995.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/90000000/89800000/89794800/89794757/1df4120a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Strasburg

[](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

10/10

Exceptional

(38 reviews)

"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "

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

Shannon H.

CA $218

CA $445 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91710000/91708800/91708790/w1024h677x0y3-155c8c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91710000/91708800/91708790/w448h683x288y0-c2af4a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91710000/91708800/91708790/7cee869f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91710000/91708800/91708790/88e8c653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middleburg

[](https://www.expedia.ca/Middleburg-Hotels-Spacious-Modern-Home-On-Middleburg-Horse-Farm.h91708790.Hotel-Information)

10/10

Exceptional

(17 reviews)

"We loved the huge kitchen and family room, and the location in Virginia horse country was amazing!"

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

STAN P.

CA $297

CA $695 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Middleburg-Hotels-Spacious-Modern-Home-On-Middleburg-Horse-Farm.h91708790.Hotel-Information)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/121000000/120020000/120016000/120015956/046ed95f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120020000/120016000/120015956/a3e961f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120020000/120016000/120015956/0e4bba5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/121000000/120020000/120016000/120015956/2c31be3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Riverview-Retreat-Pool.h120015956.Hotel-Information)

10/10

Exceptional

(1 review)

"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...

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

Stacy H.

CA $136

CA $572 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Riverview-Retreat-Pool.h120015956.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/a6d1f136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/396388c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/97da5da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/4181fefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester

[](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

9.4/10

Exceptional

(6 reviews)

"Nice house in a good central location. "

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

Mitchell V.

CA $270

CA $481 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/85e7a007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/8df6db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/01e432da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/52f36c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

9.0/10

Wonderful

(31 reviews)

"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "

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

Elissa S.

CA $233

CA $433 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124120000/124117800/124117792/b6a19cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/125000000/124120000/124117800/124117792/539d7c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/125000000/124120000/124117800/124117792/eac01a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124120000/124117800/124117792/e3a76194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Retreat-W-2-Living-Spaces-Scenic-Deck.h124117792.Hotel-Information)

CA $219

CA $454 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Retreat-W-2-Living-Spaces-Scenic-Deck.h124117792.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107630000/107623300/107623276/c59c6f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107630000/107623300/107623276/73468588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/108000000/107630000/107623300/107623276/7f07e242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107630000/107623300/107623276/bb9f79fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Leesburg's Old and Historic District

[](https://www.expedia.ca/Leesburg-Hotels-Quaint-Royal-Cottage-Historic-Leesburg.h107623276.Hotel-Information)

10/10

Exceptional

(10 reviews)

"Great location in a great town!"

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

Gigi D.

CA $302

CA $666 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Leesburg-Hotels-Quaint-Royal-Cottage-Historic-Leesburg.h107623276.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74600000/74600000/74599929/1ff1b413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74600000/74600000/74599929/b7aebdd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74600000/74600000/74599929/88e0e172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/75000000/74600000/74600000/74599929/23d5bc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Leesburg's Old and Historic District

[](https://www.expedia.ca/Leesburg-Hotels-The-Cottage-On-Royal-Historic-Leesburg-Home.h74599929.Hotel-Information)

9.8/10

Exceptional

(19 reviews)

"Delightful cottage, super convenient, and our host was extremely nice and attentive. "

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

Mark M.

CA $343

CA $719 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Leesburg-Hotels-The-Cottage-On-Royal-Historic-Leesburg-Home.h74599929.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/491c0c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/144b7449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/d041791b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/164fdddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester Historic District

[](https://www.expedia.ca/Winchester-Hotels-Indigo-Blue-Modern-Open-Vibe-On-Tree-Lined-Street.h75832658.Hotel-Information)

10/10

Exceptional

(13 reviews)

"Perfect for our needs for our daughter’s graduation!"

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

Chris and Michelle P.

CA $300

CA $555 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Winchester-Hotels-Indigo-Blue-Modern-Open-Vibe-On-Tree-Lined-Street.h75832658.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101300700/101300618/w624h619x0y0-deb888d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101310000/101300700/101300618/cf3b83aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101310000/101300700/101300618/09a5f3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101310000/101300700/101300618/a14e4ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Cozy-Hidden-Cottage-6-Mins-To-River-Hiking-Wineries.h101300618.Hotel-Information)

10/10

Exceptional

(10 reviews)

"The home was clean and beautifully decorated. "

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

Preeti r.

CA $293

CA $633 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Cozy-Hidden-Cottage-6-Mins-To-River-Hiking-Wineries.h101300618.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/9c57473e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/beb9f8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/0a99747a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/c262f123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"

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

Vinod B.

CA $112

CA $420 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112440000/112430500/112430469/d099de91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112440000/112430500/112430469/0241069a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112440000/112430500/112430469/59752003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112440000/112430500/112430469/608dfda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Harpers-Ferry-Escape-W-Hot-Tub.h112430469.Hotel-Information)

10/10

Exceptional

(12 reviews)

"Beautiful scenery! Beautiful home! Wonderful hosts!"

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

Brian S.

CA $270

CA $582 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Harpers-Ferry-Escape-W-Hot-Tub.h112430469.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78830000/78823900/78823844/a4900a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78830000/78823900/78823844/cd9ad7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78830000/78823900/78823844/db0bfe55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78830000/78823900/78823844/6c9fd86b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Spacious-Home-Steps-From-Main-St-And-Shenandoah-NP-With-Firepit-Large-Backyard.h78823844.Hotel-Information)

9.8/10

Exceptional

(18 reviews)

"Wonderful location. We were able to walk to restaurants and had a short drive to great hiking at Shenandoah National Park. "

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

Mary F.

CA $191

CA $518 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Front-Royal-Hotels-Spacious-Home-Steps-From-Main-St-And-Shenandoah-NP-With-Firepit-Large-Backyard.h78823844.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123130000/123128300/123128224/10c42ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123130000/123128300/123128224/93741415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123130000/123128300/123128224/eff16e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123130000/123128300/123128224/bbd1f182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Charming-Lodge-W-Stone-Patio.h123128224.Hotel-Information)

10/10

Exceptional

(7 reviews)

CA $215

CA $472 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Charming-Lodge-W-Stone-Patio.h123128224.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/5bcbbbaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/221f553f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/0f3fa7e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/b0176d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.Hotel-Information)

10/10

Exceptional

(42 reviews)

"Wonderful house and town! Loved every minute of our trip! "

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

MaryAnn G.

CA $207

CA $565 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/32fe1fbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/8a0bbbc2.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/114000000/113280000/113270800/113270721/706c1a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/aba028a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stephens City

[](https://www.expedia.ca/Stephens-City-Hotels-3BDR.h113270721.Hotel-Information)

9.4/10

Exceptional

(8 reviews)

"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "

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

Maureen W.

CA $162

CA $413 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Stephens-City-Hotels-3BDR.h113270721.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/a6f39c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/3689ef52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/84d2642b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/9002826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Shenandoah Farms

[](https://www.expedia.ca/Front-Royal-Hotels-25-Min-To-SNP-Forest-Views.h125448222.Hotel-Information)

CA $264

CA $742 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Front-Royal-Hotels-25-Min-To-SNP-Forest-Views.h125448222.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/b261ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/cb8a9693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/ddedca30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/w1184h883x3y0-95d19d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Linden

[](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.Hotel-Information)

10/10

Exceptional

(25 reviews)

"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "

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

Katelyn E.

CA $239

CA $512 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.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=2026-03-16&endDate=2026-03-17&regionId=184116&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)

Private vacation homes

[](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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)

Villas

[](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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

Apartments

[](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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET)

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## Top Upperville Hotel Reviews

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Nice facility, nice staff, and comfortable clean room. Superior exercise room. Suggest removing broken/non-functioning bottle fed water cooler in exercise room and having signage direct guests to water fountain “just around the corner by the elevator.“ Warm breakfast adequate and served in very comfortable, bright area. The only bill downside was fellow guests who were traveling with dogs. Despite the hotel, providing waste bags, prominently and posting signs asking guests to “pick up after your dog, please,” there was a grotesque amount of dog droppings all around the hotel exterior."

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

"Terrific room, exceptionally clean, good size, very nice staff, Good breakfast. Would highly recommend, even had free chocolate chip cookies in the lobby in the evenings. "

[](https://expedia.ca/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

"Room was clean and it was easy to check in. Breakfast in the morning was good and easy to check out also."

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

![Home2 Suites by Hilton Leesburg](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603707/8a90ec52_y.jpg)

### Home2 Suites by Hilton Leesburg

10/10 Excellent

"Spotless room, quiet and great friendly staff."

[](https://expedia.ca/Leesburg-Hotels-Home2-Suites-By-Hilton-Leesburg.h90603707.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 was great! Will go back"

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

![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg)

### Hilton Garden Inn Dulles North

10/10 Excellent

"Staff was very friendly, always enjoy this property."

[](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information)

![18th Century Stone Cottage minutes from historic Middleburg](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/b94ceda5_y.jpg)

### 18th Century Stone Cottage minutes from historic Middleburg

10/10 Excellent

"Had an excellent time staying here, it was a blend if rustic and modern. Very cozy, and had everything you'd need for a truly relaxing stay. Tim made sure everything was on point for our time at the cottage. "

[](https://expedia.ca/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information)

![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg)

### Sleep Inn & Suites Winchester near University

10/10 Excellent

"Room was clean "

[](https://expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.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

"Fantastic "

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

## Find out more about Upperville

## Upperville Vacation Homes information

| Number of reviews | 244                |
| ----------------- | ------------------ |
| Accommodation     | 231 Vacation Homes |
| Lowest Price      | CA $301            |
| Highest Price     | CA $742            |

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