How much does a Winchester vacation package cost?

Offering excellent value package deals from $278 on Expedia, you'll be surprised at how little a vacation to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Winchester?

You can typically find reduced prices and better availability in December, January and February. Take a look at our cheap Winchester vacation packages and you could land some excellent off-season deals.

How many days is enough for Winchester?

Allow around 2 days for your Winchester vacation to really discover everything that makes this place special. Explore key areas, including Old Town Winchester and College Park. Then make a beeline for major sights like Bright Box Theater and Winchester Little Theater . With a good itinerary, you'll be kept busy with room for some rest time too. Want to travel beyond Winchester? Consider squeezing in a day trip or two.

Is it worth booking a vacation package to Winchester?

Winchester is a good vacation destination with attractions like Museum of the Shenandoah Valley among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Winchester vacation promises fun for everyone.

How to find the best Winchester package deals?

Begin your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape underway.

Is it cheaper to book a Winchester vacation as a package?

You can enjoy significant savings on your next Winchester retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Winchester?

Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester trip.

How to plan a trip to Winchester?

Choose when to go: Check your schedule and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Winchester. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Winchester. Use our trip planning tool to discover Winchester: Research every aspect of your trip to Winchester with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings. Work out your trip length: Think about how much time you'd like to spend exploring Winchester. Plan your days so you can get to all the attractions and experiences you're interested in without rushing. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Winchester vacation package that brings all your bookings together. Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the best Winchester has to offer. Find all the fun things to do in Winchester with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Winchester vacation packages?

Secure your dream escape to Winchester with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up travel deals while they last.

Winchester Vacation Packages 2025/2026 from $278

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.

The Latest Winchester vacation packages

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

DoubleTree by Hilton Hotel Laurel

West Laurel

Save 100% on your flight

$278

per person

Oct 2 - Oct 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.2/10 Very Good! (1,000 reviews)

Nonsmoking room smells like pot

Reviewed on Aug 20, 2025

The Normandy Hotel

Northwest

Save 100% on your flight

$638

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Washington (WAS)

8.2/10 Very Good! (1,001 reviews)

We are happy to return to this hotel each time we visit DC. The staff is very friendly and helpful and we are always very comfortable there. The wine and cheese happy hour is a lovely treat!

Reviewed on Aug 20, 2025

Fairfield Inn by Marriott Washington D.C.

Northeast

Save 100% on your flight

$298

per person

Oct 2 - Oct 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (WAS)

8.4/10 Very Good! (1,018 reviews)

Everything was fine, except for the scary police event on the street…

Reviewed on Aug 20, 2025

InterContinental Washington D.C. - The Wharf by IHG

The Wharf

Save 100% on your flight

$732

per person

Oct 2 - Oct 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (WAS)

9.4/10 Exceptional! (1,012 reviews)

The Wharf is a beautiful area of DC. This hotel is very nice, fancy yet understated. Our room was clean, large and comfortable. Valet parking was a plus. Walkable to great restauranta and to The Anthem. A great concert venue. Our stay was lovely.

Reviewed on Aug 18, 2025

The St. Gregory Hotel

Downtown Washington D.C.

Save 100% on your flight

$372

per person

Oct 29 - Nov 1

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Washington (WAS)

8.6/10 Excellent! (1,005 reviews)

Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug 12, 2025

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Winchester Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA

Fully refundableReserve now, pay when you stay

$103 nightly

$112 total

Sep 1 - Sep 2

Total includes taxes and fees

9.2/10 Wonderful! (2,133 reviews)

"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on Aug 19, 2025

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza, Winchester, VA

Fully refundableReserve now, pay when you stay

$79 nightly

$86 total

Sep 14 - Sep 15

Total includes taxes and fees

9/10 Wonderful! (1,324 reviews)

"easy to get to, close to where I needed to be."

Reviewed on Aug 19, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester, VA

Fully refundable

$85 nightly

$92 total

Sep 7 - Sep 8

Total includes taxes and fees

9/10 Wonderful! (1,002 reviews)

"Bed comfort"

Reviewed on Aug 12, 2025

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.

Things to do in and around Winchester

Winchester, Virginia, offers a perfect blend of outdoor adventures and cultural experiences. Tour options abound, showcasing the area's rich history, while art celebrations and special events provide vibrant entertainment throughout the year. Don't miss the thrilling outdoor activities, especially during the Halloween season, when the town embraces festive fun. Whether you're exploring recreational areas or hitting the slopes for some skiing, Winchester promises an unforgettable vacation filled with adventure and scenic beauty.

Shopping

In Winchester, you can shop at Apple Blossom Mall for a variety of stores and entertainment. For fresh produce, visit Nalls Farm Market. If you're up for a drive, check out Apple Valley Square Shopping Center for more shopping options with a family-friendly atmosphere.

Recreation

Enjoy a round of golf at Rock Harbor Golf Course, where the scenic views and outdoor ambiance create a perfect retreat. Unwind at Jim Barnett Park, a serene space for relaxation and wellness activities. For a cultural experience, catch a show at Bright Box Theater, ideal for family entertainment.

Adventure

Experience the thrill of racing at Summit Point Motorsports Park, located 11 miles from Winchester. Enjoy family-friendly outdoor adventures at Watermelon Park Campground, 13 miles away. For scenic hiking, explore Tuckers Lane Trailhead, 20 miles from Winchester, where adventure and nature intertwine beautifully.

Nightlife

Winchester's nightlife offers a vibrant mix of bars and entertainment. Visit The Loudoun Street Tavern for local brews and live music, or stop by 50/50 Taphouse for a great selection of craft beers. Don't miss out on the lively atmosphere at The Bright Box Theater for unique performances.

*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 ideal destination for outdoor enthusiasts and history buffs alike, offering a mix of scenic beauty and cultural experiences. Explore historic houses, picturesque lakes, and significant historic sites. Visitors can delve into the intriguing Winchester Mystery House, visit the local museum, and enjoy family-friendly activities. Whether you're seeking adventure or a taste of local history, Winchester has something for everyone.

Shenandoah University: Experience the vibrant culture and rich history of Shenandoah University, a historic institution nestled in the heart of Winchester. Explore its beautiful campus and enjoy various cultural events, including concerts and art exhibitions.
Museum of the Shenandoah Valley: Discover the artistic treasures of the Museum of the Shenandoah Valley, where you can admire stunning art collections and learn about the region's history. The museum's beautiful gardens and exhibitions make it a cultural gem.
Shenandoah Valley Discovery Museum: Engage in hands-on learning and fun at the Shenandoah Valley Discovery Museum, perfect for families. This children's museum offers interactive exhibits that inspire curiosity and creativity in young minds.

Best time to go to Winchester

The best time to visit Winchester is dependant 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.