Upperville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Vacation Rentals in Upperville

The Oculus - Huge Cabin with a Hot Tub!
Terrace/patio

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"The place was big and very roomy and comfortable. Very clean .. very nice. "
The price is R$ 532
R$ 2.316 total
includes taxes & fees
9 Oct - 10 Oct
The Oculus - Huge Cabin with a Hot Tub!
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

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

9.2 out of 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."
The price is R$ 883
R$ 2.281 total
includes taxes & fees
6 Oct - 7 Oct
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

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

10.0 out of 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!"
The price is R$ 532
R$ 1.943 total
includes taxes & fees
8 Oct - 9 Oct
Blue Ridge Getaway - Sunset Views, A.T. Access
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Property grounds

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

10.0 out of 10, Exceptional, (46)
"Beautiful area"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (100)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
The price is R$ 1.034
R$ 3.144 total
includes taxes & fees
20 Oct - 21 Oct
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Beautifully Restored Log Cabin in Bluemont, VA
TV, fireplace, books

Beautifully Restored Log Cabin in Bluemont, VA

10.0 out of 10, Exceptional, (39)
"We had a blast here. Great cabin and great location!"
Beautifully Restored Log Cabin in Bluemont, VA
Newly renovated Farm cottage with Mountain views
Outdoor dining

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (36)
"Can’t say enough about Mint Cottage. Wonderfully furnished, immaculately clean, situated on an absolutely lovely rural property (the wildflower meadow is amazing!) Host Christine is attentive and immediately responsive. Thank you for the great stay!"
The price is R$ 851
R$ 1.720 total
includes taxes & fees
5 Oct - 6 Oct
Newly renovated Farm cottage with Mountain views
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (94)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (47)
"What a peaceful place and wonderful views."
The price is R$ 1.466
R$ 2.116 total
includes taxes & fees
26 Oct - 27 Oct
18th Century Stone Cottage minutes from historic Middleburg
Wild Hare Cottage
2 bedrooms, WiFi

Wild Hare Cottage

10.0 out of 10, Exceptional, (7)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
The price is R$ 746
R$ 1.246 total
includes taxes & fees
29 Oct - 30 Oct
Wild Hare Cottage
The Apple Mountain House
Dining

The Apple Mountain House

9.6 out of 10, Exceptional, (4)
"Amazing place to relax."
The price is R$ 1.138
R$ 2.564 total
includes taxes & fees
28 Oct - 29 Oct
The Apple Mountain House
Silo Tiny House Cabin
1 bedroom, iron/ironing board, free WiFi, bed sheets

Silo Tiny House Cabin

9.6 out of 10, Exceptional, (7)
"Heated mattress was the best. Thank you! "
The price is R$ 934
R$ 1.590 total
includes taxes & fees
7 Oct - 8 Oct
Silo Tiny House Cabin
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Dining

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (74)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is R$ 551
R$ 1.478 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (18)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is R$ 718
R$ 1.233 total
includes taxes & fees
5 Oct - 6 Oct
Apple Mountain Retreat
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Exterior

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

9.2 out of 10, Wonderful, (61)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
The price is R$ 819
R$ 1.456 total
includes taxes & fees
6 Oct - 7 Oct
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terrace/patio

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

9.8 out of 10, Exceptional, (23)
"Most enjoyable two night stay. Wish we had the time to spend more time in this lovely house and properity."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Fridge, microwave, oven, stovetop

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

9.4 out of 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!!"
The price is R$ 1.424
R$ 2.260 total
includes taxes & fees
29 Oct - 30 Oct
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Exterior

Whitetail Cabin | Couple`s Retreat w/ Hot Tub

10.0 out of 10, Exceptional, (19)
"We had a fantastic time staying at this property for the weekend."
The price is R$ 788
R$ 1.990 total
includes taxes & fees
15 Oct - 16 Oct
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Terrace/patio

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

9.2 out of 10, Wonderful, (239)
"Very nice property everything was excellent."
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (259)
"Great Property"
Breathtaking View with an Indoor Pool
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Very nice property. "
Pam 1-night trip
Posted 17 hours ago
Comfort Inn & Suites Winchester

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.

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.