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Our top choices for Upperville hotels

Hilton Garden Inn Haymarket

Hilton Garden Inn Haymarket
3.0 star property
Haymarket
9.4 out of 10, Exceptional, (271 reviews)
"Nice hotel in a hallmark town "
United States
Diane
The price is £141
includes taxes & fees
13 Mar - 14 Mar
Hilton Garden Inn Haymarket

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (133 reviews)
"Beautiful property and excellent food."
United States
Paula
Inn at Evergreen

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1,001 reviews)
"Staff was very courteous "
United States
Crystal
The price is £57
includes taxes & fees
17 Mar - 18 Mar
Rodeway Inn & Suites Charles Town

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
Charles Town
8.0 out of 10, Very good, (1,000 reviews)
"Nice place to stay"
United States
Cynthia
The price is £56
includes taxes & fees
8 Mar - 9 Mar
Days Inn by Wyndham Charles Town/Harpers Ferry

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,006 reviews)
"Great hotel!"
United States
CHARLES
The price is £103
includes taxes & fees
10 Mar - 11 Mar
The George Washington Hotel, A Wyndham Grand Hotel

Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (50 reviews)
"Unfortunately we did not get to spend lots of time on the property (other than sleeping and breakfast), but everything was great and we will definitely try to come back and spend more time at the Goodstone. "
United States
Conny
Goodstone Inn & Restaurant

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (442 reviews)
"Excellent accommodations and breakfast. "
United States
William
The price is £133
includes taxes & fees
12 Mar - 13 Mar
The Carriage Inn B&B

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (1,000 reviews)
"Amazing stay! "
Canada
Arzoo
The price is £103
includes taxes & fees
15 Mar - 16 Mar
Hampton Inn by Hilton Gainesville-Haymarket

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (817 reviews)
"Great stay!"
United States
Rene
The price is £87
includes taxes & fees
15 Mar - 16 Mar
SpringHill Suites by Marriott Winchester

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern
4.0 star property
Downtown
9.6 out of 10, Exceptional, (425 reviews)
"Amazing hotel, very cozy cottages"
United States
Babak
The Red Fox Inn & Tavern

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,283 reviews)
"Very Friendly staff and clean rooms! "
United States
Kayla
The price is £89
includes taxes & fees
8 Mar - 9 Mar
La Quinta Inn & Suites by Wyndham Winchester

Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville
2.5 star property
Gainesville
6.2 out of 10, (505 reviews)
"The room was clean, the staff is very helpful and nice and the owner do everything he can to make everyone comfortable here"
United States
James
The price is £77
includes taxes & fees
8 Mar - 9 Mar
Extended Stay America Select Suites Gainesville

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (939 reviews)
"Very clean room, nice friendly staff, delicious food at the restaurant "
United States
Julie
The price is £87
includes taxes & fees
10 Mar - 11 Mar
Courtyard by Marriott Winchester

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG
2.5 star property
Charles Town
9.2 out of 10, Wonderful, (1,004 reviews)
"Clean room nice staff and very convenient. "
United States
Kimberly
The price is £87
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Charles Town by IHG

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North
3.0 star property
Ashburn
8.4 out of 10, Very good, (1,002 reviews)
"Clean room,.nice staff, large walk-in shower, coffee maker and mini fridge! Great price, saved 20 bucks online with Expedia app! I will definitely come back for another "staycation" "
United States
Patrick
The price is £82
includes taxes & fees
29 Mar - 30 Mar
Hilton Garden Inn Dulles North

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,002 reviews)
"Great stay!"
United States
gary
The price is £74
includes taxes & fees
15 Mar - 16 Mar
Country Inn & Suites by Radisson, Winchester, VA

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (674 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is £143
includes taxes & fees
10 Mar - 11 Mar
Hillbrook Inn

Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (384 reviews)
"Room was awesome, amazing experiences at the resort and really great customer service"
United States
Anwar
The price is £545
includes taxes & fees
8 Mar - 9 Mar
Salamander Resort And Spa

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (176 reviews)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is £158
includes taxes & fees
15 Mar - 16 Mar
L'Auberge Provencale Inn & Restaurant

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,005 reviews)
"Great stay"
United States
Lori
The price is £74
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Winchester Se-Historic Gateway by IHG
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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Stay near popular Upperville attractions

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

Hiking Sky Meadows State Park...
Photo by Michael Gibson
Open Photo by Michael Gibson

Top Upperville Hotel Reviews

More cheap stays in Upperville

Frequently asked questions

What is the best area to stay in Upperville?
The best area to stay in Upperville is directly within the village centre, as it offers the most convenient access to local attractions and a quintessential experience of the area.

Upperville's village centre is small and picturesque, primarily centred around the intersection of John S. Mosby Highway (Route 50) and Trappe Road. This area is characterised by its historic stone and brick buildings, many of which house boutique shops, art galleries, and acclaimed dining establishments. The iconic Trinity Episcopal Church is a prominent landmark, and the area is surrounded by rolling hills and horse farms, providing a scenic backdrop.

Couples looking for a romantic and sophisticated getaway will find the village centre particularly appealing. You'll be within easy walking distance of gourmet restaurants for intimate dinners and unique shops for browsing. The relaxed pace and beautiful surroundings make it ideal for a quiet escape.

For those interested in equestrian activities, staying in the village centre provides excellent access to the renowned Upperville Colt & Horse Show grounds, which are just a short drive away.
When is the best time to go to Upperville?
The best time to go to Upperville is during the spring (late April to early June) and autumn (September to October) months, when the weather is mild and the natural beauty of the Virginia countryside is at its peak.

Spring brings blooming dogwoods and redbuds, making it an ideal time for outdoor activities like horseback riding or visiting local vineyards. The Upperville Colt & Horse Show, a significant equestrian event, usually takes place in early June, drawing many visitors to the area.

Autumn offers stunning foliage as the trees along the Blue Ridge Mountains turn vibrant shades of red, orange, and gold. This season is great for scenic drives, exploring the historic villages nearby, and enjoying the numerous harvest festivals and farm-to-table dining experiences.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Upperville.
How can I save on a Upperville hotel booking with Expedia?
Members always get our best prices. Find our best Upperville hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Upperville hotel?
Prices for hotels in Upperville often vary, but you can find a great deal from £56 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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