Title: Upperville Vacation Rentals from CA $323: Short-Term Rentals for 2025 | Expedia.ca

  

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# Upperville Vacation Rentals

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## Check prices for these dates

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Upperville

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/3fb00335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/ba83a961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/b0328aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/43f68831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oculus - Huge Cabin with a Hot Tub!

Harpers Ferry

9.6/10

Exceptional

(24)

"The place was big and very roomy and comfortable. Very clean .. very nice. "

CA $140

CA $610 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-The-Oculus-Huge-Cabin-In-The-Woods-With-A-Hot-Tub.h89354942.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/f943ceaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/82afadcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/008ff9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, table tennis](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/8adae47f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Harpers Ferry

9.2/10

Wonderful

(12)

"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."

CA $232

CA $604 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Charming-3-Bedroom-House-With-Firepit-And-Game-Room-In-Gorgeous-Harpers-Ferry.h112582495.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/58000000/57990000/57981800/57981735/4acf1643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/58000000/57990000/57981800/57981735/4492a9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57990000/57981800/57981735/ef573c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/58000000/57990000/57981800/57981735/9f77b6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Front Royal

10/10

Exceptional

(46)

"Beautiful area"

[](https://www.expedia.ca/Front-Royal-Hotels-Bear-Mountain-Lodge-Shenandoah-Mountains-Skyline-Drive.h57981735.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/2791d502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/5c391e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/ec01e8fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/0aaeb11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Linden

10/10

Exceptional

(95)

"Very nice relaxing getaway, quite how do you spell quiet and serene location. "

[](https://www.expedia.ca/Front-Royal-Hotels-Whiskey-Hill-Cabin-A-Mountain-Getaway-In-Virginia-Wine-Country.h67385431.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30010000/30009300/30009218/22b0bbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30010000/30009300/30009218/cc4083e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30010000/30009300/30009218/4d4d4489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/31000000/30010000/30009300/30009218/53cbc09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry

9.8/10

Exceptional

(100)

"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."

CA $244

CA $791 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Large-Groups.h30009218.Hotel-Information)

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

![Interior](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/c88c2512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/e6d9ee21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71520000/71515000/71514925/61358970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Harpers Ferry

10/10

Exceptional

(59)

"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"

CA $142

CA $517 total

includes taxes & fees

Oct 13 - Oct 14

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

![TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92340000/92335200/92335119/7eb0f373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92340000/92335200/92335119/d06670b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/93000000/92340000/92335200/92335119/1502e573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92340000/92335200/92335119/9f208ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautifully Restored Log Cabin in Bluemont, VA

Bluemont

10/10

Exceptional

(39)

"We had a blast here. Great cabin and great location!"

[](https://www.expedia.ca/Bluemont-Hotels-Beautifully-Restored-Log-Cabin-In-Bluemont.h92335119.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/15fd4469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/2f2ce964.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)

![Interior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/8e6ba5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Newly renovated Farm cottage with Mountain views

Strasburg

10/10

Exceptional

(36)

"Very clean cottage with well-stocked kitchen with a great outdoors area for grilling and hanging out. Quiet relaxing location way up off the road. The hosts were unobtrusive but available. We have already recommended this cottage to our immediate family for future stays. "

CA $223

CA $455 total

includes taxes & fees

Oct 15 - Oct 16

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

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/5b26230e.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)

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.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)

### Wild Hare Cottage

Purcellville

10/10

Exceptional

(7)

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

CA $195

CA $326 total

includes taxes & fees

Oct 29 - Oct 30

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

![Exterior detail](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/70f73403.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)

![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/ef95a95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Harpers Ferry

10/10

Exceptional

(75)

"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "

CA $160

CA $410 total

includes taxes & fees

Oct 14 - Oct 15

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

![Dining](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/25a6efcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/563df015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/a2c39a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/2032cec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Apple Mountain House

Front Royal

9.6/10

Exceptional

(4)

"Amazing place to relax."

CA $359

CA $759 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100870000/100865000/100864952/cfe66953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100870000/100865000/100864952/cb778f3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100870000/100865000/100864952/86846831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100870000/100865000/100864952/e0cc9be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silo Tiny House Cabin

Harpers Ferry

9.6/10

Exceptional

(7)

"Heated mattress was the best. Thank you! "

CA $245

CA $417 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Silo-Tiny-House-Cabin.h100864952.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)

![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)

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

![Exterior](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/48aeb310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apple Mountain Retreat

Linden

10/10

Exceptional

(18)

"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "

CA $188

CA $323 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Linden-Hotels-Cozy-Spacious-Full-Basement-In-Single-Family-Home-On-Apple-Mountain.h104052857.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275454/85ed8f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275454/1f31e574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275454/97cfbfe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275454/eb04890a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Harpers Ferry

9.2/10

Wonderful

(61)

"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"

CA $215

CA $382 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Hot-Tub.h60275454.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/2b9acd11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e29f28d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/5ce5fa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Middleburg

10/10

Exceptional

(47)

"What a peaceful place and wonderful views."

CA $383

CA $555 total

includes taxes & fees

Nov 3 - Nov 4

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

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106630000/106625200/106625175/a82ca8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106630000/106625200/106625175/f02d3d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106630000/106625200/106625175/a460d78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106630000/106625200/106625175/a222330c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

Charles Town

9.8/10

Exceptional

(23)

"Loved this home in the riverfront! Perfect Fourth of July Getaway for the whole family. "

[](https://www.expedia.ca/Charles-Town-Hotels-18-Private-Acres-And-800-Feet-Of-Glorious-Shenandoah-River-Frontage-WiFi.h106625175.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/be781d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/1551784a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/1d57d1e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/85823fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breathtaking View with an Indoor Pool

Bluemont

9.8/10

Exceptional

(259)

"Great Property"

[](https://www.expedia.ca/Bluemont-Hotels-Breathtaking-Views-With-An-Indoor-Private-Pool.h19651347.Hotel-Information)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/bc2bc4b0.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/93000000/92170000/92168300/92168268/b1e90ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/0ec95494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Harpers Ferry

9.4/10

Exceptional

(26)

"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"

CA $353

CA $568 total

includes taxes & fees

Nov 5 - Nov 6

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/533e235c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/1b864f69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/ad31a208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/4e14b14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whitetail Cabin | Couple\`s Retreat w/ Hot Tub

Linden

10/10

Exceptional

(20)

"We had a fantastic time staying at this property for the weekend."

CA $195

CA $508 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Linden-Hotels-Whitetail-Cabin-Couples-Retreat-W-Hot-Tub.h91195541.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27020000/27014300/27014263/47cb5e5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27020000/27014300/27014263/72a627b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27020000/27014300/27014263/2713db91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27020000/27014300/27014263/18a5cefc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Front Royal

9.2/10

Wonderful

(239)

"Very nice property everything was excellent."

[](https://www.expedia.ca/Front-Royal-Hotels-Rustic-Mountain-Log-Cabin-Perched-On-A-Cliff-Side-Above-The-Shenandoah-River.h27014263.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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## Top Upperville Hotel Reviews

![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg)

### Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!"

[](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

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

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

10/10 Excellent

"2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. "

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

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

### SpringHill Suites by Marriott Winchester

10/10 Excellent

"Convenient "

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

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Great location."

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

![Microtel Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg)

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean place good price"

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

![Red Roof Inn Leesburg, VA](//images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg)

### Red Roof Inn Leesburg, VA

10/10 Excellent

"It was a good cozy stay for after visiting for a wedding and I would stay here again. "

[](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information)

![Clarion Inn Harpers Ferry - Charles Town](//images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90_y.jpg)

### Clarion Inn Harpers Ferry - Charles Town

10/10 Excellent

"way better than we expected in all areas. great service , very clean , very nice attached restaurant "

[](https://expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information)

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

### Lansdowne Resort and Spa

10/10 Excellent

"Hotel has a lot of amenities, we also used the spa, pool and hot tub. Also took one of the free workout classes."

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

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

### Comfort Inn & Suites Winchester

10/10 Excellent

"Clean room and spacious"

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

## Find out more about Upperville

**Everything you need to know about** **Upperville** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upperville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Upperville vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Upperville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upperville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upperville vacation rentals we have selected for you start as low as CA $323 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Upperville rentals**

At Expedia, we put the best Upperville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upperville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upperville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upperville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Upperville

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-   [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Vacation Homes in Upperville](https://expedia.ca/Upperville-Private-Vacation-Homes.d184116-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Upperville](https://expedia.ca/Upperville-Cottages.d184116-aaCottages.Travel-Guide-Accommodation)
-   [Cabin Rentals in Upperville](https://expedia.ca/Upperville-Cabins.d184116-aaCabins.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)
-   [B&B in Upperville](https://expedia.ca/Upperville-Bed-And-Breakfast.d184116-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Motels in Upperville](https://expedia.ca/Upperville-Motels.d184116-aaMotels.Travel-Guide-Accommodation)
-   [Chalets in Upperville](https://expedia.ca/Upperville-Chalets.d184116-aaChalets.Travel-Guide-Accommodation)
-   [Guest Houses in Upperville](https://expedia.ca/Upperville-Guest-Houses.d184116-aaGuestHouses.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)
-   [Resorts in Upperville](https://expedia.ca/Upperville-Resort-Hotels.d184116-aaResortHotels.Travel-Guide-Accommodation)
-   [Lodges in Upperville](https://expedia.ca/Upperville-Lodges.d184116-aaLodges.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?

> Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

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

> [Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex](https://www.expedia.ca/Harpers-Ferry-Hotels-Large-Groups.h30009218.Hotel-Information): This vacation home rental outside of Upperville is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a hot tub.

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

> Choose from 5 Expedia vacation rentals in Upperville for a memorable vacation.

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

> While exploring the area, visit family-friendly sights like Great Country Farms, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

### What are vacation rentals like in Upperville?

> Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

### Expedia's Latest Trends

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Flights

-   [Flights to Hampton](https://expedia.ca/Cheap-Flights-To-Hampton.d6067.Travel-Guide-Flights)
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-   [Flights to Virginia Beach](https://expedia.ca/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
-   [Flights to Alexandria](https://expedia.ca/Cheap-Flights-To-Alexandria.d5980.Travel-Guide-Flights)
-   [Flights to Fairfax](https://expedia.ca/Cheap-Flights-To-Fairfax.d8062.Travel-Guide-Flights)
-   [Flights to Roanoke](https://expedia.ca/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights)
-   [Flights to Syria](https://expedia.ca/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights)
-   [Flights to Fredericksburg](https://expedia.ca/Cheap-Flights-To-Fredericksburg.d8145.Travel-Guide-Flights)
-   [Flights to Charlottesville](https://expedia.ca/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights)

Activities

-   [Things to do in Virginia Beach](https://expedia.ca/Things-To-Do-In-Virginia-Beach.d10271.Travel-Guide-Activities)
-   [Things to do in Norfolk](https://expedia.ca/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities)

Packages

-   [Virginia Beach Vacations](https://expedia.ca/Virginia-Beach.d10271.Destination-Travel-Guides)
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Vacation Rentals

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

General

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## Go further with the Expedia app

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Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFJElEQVR4Xu3cPXbbOhBAYfqoUJklcCleGrw0LkVLSKnCx4jmBwOQgi1PkZwT+d4m1BDAp46h4/eW+g9ajoO/EUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSDcj7cmiVUbGb23KWPy4yL/W3LbiNfGmMer5RAtFAxkDaKALRQMZA2ih6VqT0T1WQW2+39S+C3HJkWX7ZkquNTnL9W1ZF+7NANJAeiAYCUkFA/Mb49F5lOiJD7UT/KBv7qhXE5hEIiAQCsoCAtEX9coL00as90O/yr1JBQEBA2qJ+CWIXICBJpMoz3t+nJ6k7vmKDgIDcBQICAvIY6e2RTdx9PhqRCASkgmggpX8CsUBA6hHZt9pa3a4nfj06VPrJIJPRodJPBpmMDpV+MshkdKj0k0Emo0OlnwwyGR0q/WSQyehQ6ScPyGfpid7FDvhVP4bj9Bn/VSAgnwXSAwH5LJDe8yJ64mab757esqA/472L3dMXcf+ht6+KQEA0EBCQWBWBgPiNj+GXufrarUGn+KG3nuiNbny7CEQDAQHpowrSJv0S5OciS9sud2ztWK0XQaqduNlwlcHb4v8N1Fk2aiVOAgEBWWXwtoCAWCVOAgF51NU3y3Z9646/CTzse6skkAoC8jCQCgLysP8IeZft/ootd+wZHyeOq/wZrw/01eY68i72VSIQEBCbg4CAgFh7ZHzFjpGmD3TpJO/TukqRYZUiV3nsX+RjiVNA5CYIiAYCIh9LnAIiN0G+enrr9nFVjHrugoBoICAgQyAg30O8t0Wf3pvsC9dfxK82PMlAX8SXYeMQCAgICAgIyNgekRriJ/r7dJUTa720E+9cHekqGekXjkBAQOw2yCpTEBCQO0T/rx2vdqImyIfccddXaeMq/XaOLPZVIhANBATEAhkD0UC0V71ja337ZncUKe2BrqtWuxhHWvGPMumXIHYBAmIV/yiTfgliFyAgVvGPMumXz4NUO3FxpNaLffLHfo0T5bFf3bWV/aucfbALpIKA6AgE5C6Q+uMRf8a/yPVVrla5ku3LgOgzXv+B2YtVbaN/O1nlgYCAtFUgFWQBAdkhVdb2B7qs7a/Ynm6Xx36NZ7yPxm+nldgEItebXIGAgIBIJTaByPUmVz8XmT+95WfXi7hXOdFXTUcv4p5vR4LcnTgZgWjTEycjEG164mQEok1PnIxAtOmJkxGINj1xMvoWUuOBvsmiWuMZryeOq/QZXxvio49YdQHZrQLRQEBAJJDX3SqQyaN6bXfadhm9G9pW+Ylj/u2GQEBAdsICAhKBgEzqrj/Q9ycq4qu0bbjpIwlEA9kHIvlIAtFA9oFIPpKeEnkfVmirTON9+laM/Bm/hOtfRUdeiW0gICAX+QMEpFViGwiIIKV/0hN1pP+a7K12z08826e+cTKSQEBAQCSQw0gCARlPPAcivbTFlqw6IJGOvvgJNwgICIgE0gIBmSA1XrE3mfr2/cg3ajryfCSB9BEICAgICMgjxLe33+8SRLf3VYP7EaPRlUBAQEBAQEoFsSvpiPQEqbJdX7E3c7Vx1d59baPTbglID0QD0REISAUZ+8HIvtXm++2avmLrb1x7perfBMZk5IFoIGOrzUFsjQSigYytNgexNdJTIn8vkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaR6HuQPde4LD2xmGLkAAAAASUVORK5CYII=)