Upperville, VA

Travel Guide

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.
A lush green field with wildflowers and a distant view of rolling hills and a red-roofed building.
A grassy path leading through a field with a forested hill in the background.
A gravel path flanked by wooden fences and surrounded by trees.
A narrow dirt path through a grassy field with wildflowers and tall grasses.
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
$245 nightly
The price is $280 total per night from Nov 1 to Nov 2
$280 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Lansdowne Resort and Spa
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
$130 nightly
The price is $148 total per night from Oct 28 to Oct 29
$148 total
Oct 28 - Oct 29
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."

Reviewed on Oct 7, 2026

The George Washington Hotel, A Wyndham Grand Hotel
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
$85 nightly
The price is $95 total per night from Nov 1 to Nov 2
$95 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
"Everything was good"

Reviewed on Oct 9, 2026

TRU By Hilton Winchester
See all 761 properties in Upperville
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.
Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.

Bluemont VA
Stay at this cabin in Bluemont. Enjoy laundry facilities and air conditioning. Popular attractions Cool Spring and Holy Cross Abbey are located nearby.
8/10 Very Good! (5 reviews)
"We stayed for a night for a wedding nearby at a winery and it was perfect! Very cute and relaxing, we will definitely return in the future! The place was accurately described and same as the photos. It’s perfect for a weekend getaway!"

Reviewed on Sep 14, 2026

Your Peaceful Getaway in the Blue Ridge.
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Harpers Ferry WV
Book a stay at this family-friendly cabin in Harpers Ferry. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah Lake Beach and ...
10/10 Exceptional! (107 reviews)
"This home presented as pictured and described. Access was easy and the cabin was very clean and comfortable.The bed in the front bedroom was very comfortable."

Reviewed on Oct 3, 2026

~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal VA
Stay at this vacation home in Front Royal. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah River and Bing Crosby Stadium are ...
10/10 Exceptional! (43 reviews)
"A very warm welcome. Easy access to Shenandoah parks."

Reviewed on Sep 26, 2026

Mountain View Bungalow in Front Royal
See all properties in Upperville
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.

Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
See properties

Frequently asked questions

When is the best time to visit Upperville?
The best time to visit Upperville is from April through June. Travelers looking for a more relaxed experience with fewer crowds and potentially better value might consider visiting during the cooler months of November through January.
What is Upperville known for?
Upperville is known for Upperville Park, a central green space that provides travelers with opportunities for outdoor activities and relaxation. It serves as a key local landmark.
What is a good itinerary length for Upperville?
A good itinerary length for Upperville is one to two days to explore Upperville Park and enjoy local North American cuisine. An extended stay of three days allows for a more leisurely pace to experience the area's natural beauty and relax in this charming destination.
What are the top things to do in and around Upperville?
In Upperville, explore Upperville Park, a natural area of interest.
Can I book a refundable hotel in Upperville?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Upperville by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Upperville with Expedia?
Expedia makes it easier to plan your Upperville trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Upperville?
The best choice depends on your travel style. Hotels in Upperville can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Upperville trip on Expedia?
Once you've booked your Upperville trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Upperville trip?
Expedia offers customer support before, during, and after your Upperville trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Upperville?
If it's your first trip to Upperville, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Upperville hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Upperville hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Upperville

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A lush green field with wildflowers and a distant view of rolling hills and a red-roofed building.

Boyce

A lush green field with wildflowers and a distant view of rolling hills and a red-roofed building.

Paris

A vineyard with rows of grapevines, a winding road, and a distant view of rolling hills and a cloudy sky.

Bluemont

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