Name: The George Washington Hotel, A Wyndham Grand Hotel
Price range: CA $178
Rating: 9.4

Your Winchester Vacation

The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.

The Westin DC Downtown

Downtown Washington D.C.

CA $551

per person

Jun 5 - Jun 7

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Baltimore (BWI)

8.8/10 Excellent! (1,009 reviews)

I would highly recommend this hotel to anyone. The staff are nice and helpful when we had questions. The staff at Root &Vine when we order pizza's to take back to our room. The sercurity guards in the lobby would always say hi and ask how you are doing. The room was amazing and we enjoyed the view from our room.

Reviewed on Apr 10, 2026

Kellogg Conference Hotel at Gallaudet University

Northeast

CA $1,020

per person

Jul 2 - Jul 5

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to Baltimore (BWI)

8.2/10 Very Good! (1,007 reviews)

It was so nice, and it is a college campus, so it is really safe. Pet-friendly and good breakfast. Parking is way too expensive. No need to charge $50 a night when there is plenty of parking.

Reviewed on Apr 4, 2026

YOTEL Washington DC

Northwest

CA $2,158

per person

Jun 30 - Jul 5

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Baltimore (BWI)

8.2/10 Very Good! (2,372 reviews)

Our stay at the Yotel in Washington DC was great. The staff are extremely knowledgeable and friendly. They go above and beyond to assist. 💕 I would have liked to use the pool—however I’ll have to come back! Check in/out are a breeze, no waiting in line unless there’s a question or issue. The only real negative is the lack of a coffee machine in the room. This would really make our stay exceptional. There is limited coffee provided on the 2nd floor—however most hotels have this accessible at all times. We were able to get a mini fridge which I greatly appreciated as I was travelling with two kids. Parking is easy and underneath the hotel, which made it easy to transport our items. The location is minutes from Union station and about 10-15 min from the Smithsonian museums. Great location! Thank you for a great stay.

Reviewed on Apr 25, 2026

The Churchill Hotel near Embassy Row

Northwest

CA $970

per person

Jul 2 - Jul 5

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to Baltimore (BWI)

8.8/10 Excellent! (1,007 reviews)

Giving it a three star because there was no A/C in the room and it was quite hot in DC. The location was great as it was located right in the heart of DC. The staff was friendly and helpful but we didn’t realize that breakfast was NOT complimentary, so ultimately I didn’t even eat breakfast but that’s not a big deal. Overall, it was a decent experience. Location was ideal, but A/C was not working

Reviewed on Apr 25, 2026

Omni Shoreham Hotel

Northwest

CA $1,279

per person

Jul 2 - Jul 5

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to Baltimore (BWI)

9/10 Wonderful! (2,240 reviews)

The property was beautiful and very comfortable and accommodating. The staff were so friendly and helpful and kind throughout our stay there. At one point, I injured myself by tripping on the stairs and the security team could not have been more helpful and concerned for my well-being.

Reviewed on Apr 19, 2026

Things to do in and around Winchester

Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers alike. Visitors can enjoy various recreational opportunities, including scenic hikes and golf vacations. The area also offers educational experiences and options for skiing during the winter months. Whether you're seeking a relaxing getaway or an active trip, Winchester provides a range of activities to suit every traveller's interests.

Shopping

In Winchester, you can shop at Apple Blossom Mall for a variety of stores and entertainment. Apple Valley Square Shopping Center offers local businesses in a family-friendly atmosphere. If you're up for a drive, explore Nalls Farm Market for fresh produce and unique gifts outside the city.

Recreation

Jim Barnett Park offers a tranquil escape with its lush green spaces and scenic walking trails, perfect for relaxation. For a bit more activity, head to Appleland Sports Center, where you can enjoy various recreational facilities. Rock Harbor Golf Course provides a delightful outdoor experience for golf enthusiasts.

Adventure

Experience the thrill of racing at Summit Point Motorsports Park, located 17.7km from Winchester, where adrenaline meets speed. For a fun-filled outdoor experience, head to Watermelon Park Campground, 20.9km away, perfect for family camping and adventure. Engage in an exhilarating paintball battle at North Mountain Paintball, also 17.7km from Winchester.

Nightlife

Winchester's nightlife features a vibrant atmosphere with an array of pubs and live music venues. Visit the Loudoun Street Grill for hearty meals and local brews, or enjoy live performances at the Bright Box Theater. Don't miss the laid-back vibe at the Alamo Drafthouse for a unique cinema experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Winchester

Winchester, Virginia, is an excellent destination for outdoor and adventure enthusiasts, offering stunning scenery and a rich cultural experience. Explore historic houses and places, enjoy the beauty of local lakes, and discover popular attractions such as Winchester Cathedral. Whether you're seeking family-friendly activities or a deep dive into the area's history, Winchester has something for everyone. Don't miss out on the chance to experience the charm and allure of this vibrant city.

Shenandoah University: Experience the vibrant atmosphere of Shenandoah University, a historic college nestled in Winchester. With its beautiful campus and rich cultural vibes, it's an ideal spot for leisurely strolls and soaking in the academic spirit.
Museum of the Shenandoah Valley: This artistic gem showcases the region's rich history and culture through captivating exhibits and stunning gardens. The museum's engaging displays make it a delightful destination for art enthusiasts and history buffs alike.
Shenandoah Valley Discovery Museum: Perfect for families, this children's museum offers interactive exhibits that ignite curiosity and creativity in young minds. It's a fun-filled environment where learning meets play, making it a memorable stop for visitors of all ages.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.3°F (-0.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	34.7°F (1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Average	Average
May	62.4°F (16.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	70.9°F (21.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Average	Average
September	66.9°F (19.4°C)	Light Rain	Mostly Sunny	Average	Average
October	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
November	43.5°F (6.4°C)	Light Rain	Mostly Sunny	Average	Average
December	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Winchester

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winchester.
Consider traveling to Winchester during the low season (January to March) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Winchester?

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Winchester Hotel Deals

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

Fully refundableReserve now, pay when you stay

CA $97

CA $106 total

Apr 27 - Apr 28

includes taxes & fees

8.6/10 Excellent! (1,065 reviews)

Parking was close and well lit

Reviewed on Apr 17, 2026

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

Fully refundableReserve now, pay when you stay

CA $124

CA $134 total

May 10 - May 11

includes taxes & fees

9.2/10 Wonderful! (1,445 reviews)

Great breakfast with a good selection. Friendly staff and the rooms are clean.

Reviewed on Apr 24, 2026

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

CA $178

CA $202 total

May 25 - May 26

includes taxes & fees

9.4/10 Exceptional! (1,005 reviews)

Quiet, distinctive, friendly and close to old town, a half mile walk to Patsy Cline home. Breakfast was good and staff excellent.

Reviewed on Apr 25, 2026

See all 2,081 properties in Winchester

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.