Title: Experience Winchester Vacation Book from $186 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Vacations from $186 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction), [Museum of the Shenandoah Valley](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) and [Apple Blossom Mall](https://www.expedia.com/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction). 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. ![Hyatt House BWI Airport Baltimore](https://images.trvl-media.com/lodging/104000000/103180000/103174300/103174233/d66a3891_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt House BWI Airport Baltimore Save 100% on your flight $186 per person Apr 16 - Apr 19 found 2 days ago Roundtrip flight included Atlanta (ATL) to Baltimore (BWI) 9.4/10 Exceptional! (665 reviews) Great place, great staff and breakfast. Can’t wait to stay again! Reviewed on Feb 1, 2026 ![Hilton Washington DC Capitol Hill](https://images.trvl-media.com/lodging/1000000/20000/11300/11216/da79e2b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Washington DC Capitol Hill Northwest Save 100% on your flight $373 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9/10 Wonderful! (1,002 reviews) No problems, good service Reviewed on Feb 2, 2026 ![West End Washington DC, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/25400/25371/546632c4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### West End Washington DC, Tapestry Collection by Hilton Downtown Washington D.C. Save 100% on your flight $340 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 8.6/10 Excellent! (1,000 reviews) Clean room, friendly staff Reviewed on Jan 2, 2026 ![InterContinental Washington D.C. - The Wharf by IHG](https://images.trvl-media.com/lodging/17000000/16030000/16024200/16024166/a1ea6b4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Washington D.C. - The Wharf by IHG Southwest Save 100% on your flight $522 per person Apr 3 - Apr 5 found 1 day ago Roundtrip non-stop flight included Atlanta (ATL) to Washington (DCA) 9.4/10 Exceptional! (1,005 reviews) Everything was excellent! Reviewed on Jan 25, 2026 ![The Normandy Hotel](https://images.trvl-media.com/lodging/1000000/20000/17000/16930/e5805448_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Normandy Hotel Northwest Save 100% on your flight $734 per person Apr 28 - May 3 found 17 hours ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 8.4/10 Very Good! (1,002 reviews) We enjoyed our stay at The Normandy. Reviewed on Feb 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Winchester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=DCA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Winchester ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) ![Jim Barnett park](https://images.trvl-media.com/place/6056879/c975fc72-ad57-4298-afc1-a46af23cbed9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Jim Barnett Park Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) #### ValleyHealth Winchester Medical Center Though ValleyHealth Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here. [](https://expedia.com/ValleyHealth-Winchester-Medical-Center-Winchester.d6164057.Vacation-Attraction) ## Winchester Hotel Deals ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East Winchester VA Fully refundableReserve now, pay when you stay $98 nightly $107 total Feb 8 - Feb 9 Total with taxes and fees 9.2/10 Wonderful! (2,258 reviews) Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA Fully refundableReserve now, pay when you stay $127 nightly $143 total Feb 12 - Feb 13 Total with taxes and fees 9.2/10 Wonderful! (1,002 reviews) Clean nice room Great location for restaurants Reviewed on Jan 28, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6056879) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA Fully refundableReserve now, pay when you stay $85 nightly $92 total Feb 9 - Feb 10 Total with taxes and fees 9/10 Wonderful! (1,439 reviews) Room was very clean and spacious, staff was wonderful! Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6056879) [See all 2,067 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=6056879) 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. ## Find the Best Winchester Vacation Packages ### Things to do in and around Winchester Winchester, Virginia, offers a delightful mix of outdoor adventures and cultural experiences. Visitors can explore scenic recreational areas, participate in local art celebrations, and enjoy special events throughout the year, including festive Halloween activities. The city also provides various tour options and opportunities for skiing, making it a perfect destination for those seeking adventure and education in a picturesque setting. **Shopping** In Winchester, visit [Apple Blossom Mall](https://www.expedia.com/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction) for a variety of shops and family-friendly entertainment. [Nalls Farm Market](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) offers local goods, while Apple Valley Square Shopping Center has a mix of businesses. If you're up for a drive, check out nearby shopping centers for even more options. **Recreation** Experience tranquility at [Jim Barnett Park](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction), where you can enjoy serene walks and relaxation amidst nature. For outdoor enthusiasts, [Rock Harbor Golf Course](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) offers a refreshing round of golf in a beautiful setting. Don't miss [Bright Box Theater](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) for captivating performances that bring culture and entertainment to your visit. **Adventure** Experience the thrill at [Summit Point Motorsports Park](https://www.expedia.com/Summit-Point-Motorsports-Park-Summit-Point.d6164103.Vacation-Attraction), located 11 miles from Winchester, where you can race and feel the adrenaline rush. For family camping, head to [Watermelon Park Campground](https://www.expedia.com/Watermelon-Park-Campground-Berryville.d553248621532661928.Vacation-Attraction), 13 miles away, offering outdoor fun. Don't miss the excitement at North Mountain Paintball, also 11 miles from Winchester. **Nightlife** Winchester's nightlife features cozy bars and vibrant live music spots. Visit the Bright Box Theater for eclectic performances, or unwind at the Cellar Door for craft cocktails. For a fun evening, savor local brews at the Winchester Brew Works while mingling with friendly locals. \*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 a charming destination perfect for outdoor enthusiasts and history buffs alike. Visitors can explore historic houses, scenic lakes, and significant historic sites, making it ideal for family adventures and cultural experiences. Don't miss the intriguing Winchester Mystery House and its related attractions, along with the bizarre mansion and historic estate tours, which offer a unique glimpse into the area's rich heritage. - **[Shenandoah University: ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction)** Immerse yourself in the vibrant atmosphere of Shenandoah University, a historic institution in Winchester. Explore its beautiful campus, rich traditions, and cultural events that reflect the dynamic spirit of the local community. - **[Museum of the Shenandoah Valley: ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction)** Discover the region's history and artistic heritage at the Museum of the Shenandoah Valley. This art museum features impressive exhibits, beautiful gardens, and engaging programs that highlight the area's cultural significance. - **[Shenandoah Valley Discovery Museum: ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction)** Perfect for families, the Shenandoah Valley Discovery Museum offers hands-on exhibits and interactive experiences that inspire curiosity and creativity in children. Enjoy a fun and educational visit for 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](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)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 - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Winchester. - 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. ## Winchester Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 27,300 | | Max Temp Winter | 40ºF | | Max Temp Summer | 85ºF | | Top Sights | [Museum of the Shenandoah Valley](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction), [Shenandoah Valley Discovery Museum](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) and [Bright Box Theater](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Winchester vacation package cost? ### What are the cheapest months to go to Winchester? ### How many days is enough for Winchester? ### Is it worth booking a vacation package to Winchester? ### How to find the best Winchester package deals? ### Is it cheaper to book a Winchester vacation as a package? ### When to book a vacation package to Winchester? ### How to plan a trip to Winchester? > 1. 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. > 2. 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. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) 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. > 4. 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. > 5. 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. > 6. 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](https://www.expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities) with our dedicated activity guide. ### Does Expedia offer Book Now, Pay Later Winchester vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Restaurants.0-n6164092-0-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Casino Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Casino-Hotel.0-n6164092-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with Bars in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Bar-Hotel.0-n6164092-0-tBarHotel.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Cheap-Hotels.0-n6164092-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Connecting Rooms in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Adjoining-Rooms.0-n6164092-0-tHotelswithAdjoiningRooms.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Old Town Winchester ](https://www.expedia.com/5Star-Old-Town-Winchester-Winchester-Hotels.s50-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Hot-Tubs.0-n6164092-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Balconies.0-n6164092-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Laundry Facilities in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Laundry-Facilities.0-n6164092-0-tHotelswithLaundryFacilities.Travel-Guide-Filter-Hotels) - [Gay friendly Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-LGBT-Welcoming-Hotel.0-n6164092-0-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Ski-Hotel.0-n6164092-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Luxury-Hotel.0-n6164092-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Business-Hotel.0-n6164092-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Beach Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Beach-Hotel.0-n6164092-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Old Town Winchester ](https://www.expedia.com/4Star-Old-Town-Winchester-Winchester-Hotels.s40-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels with Room Service in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Room-Service.0-n6164092-0-tHotelswithRoomService.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Wedding-Hotels.0-n6164092-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Hotels near Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - 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[Hotels near Stonewall Jackson's Headquarters ](https://www.expedia.com/Stonewall-Jacksons-Headquarters-Hotels.0-l6164032-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Hotels near Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels) - [Hotels near Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels) - [Hotels near Abram's Delight ](https://www.expedia.com/Abrams-Delight-Hotels.0-l553248621532661839-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau ](https://www.expedia.com/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University ](https://www.expedia.com/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.com/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center ](https://www.expedia.com/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Flights from Frederick County ](https://www.expedia.com/lp/flights/553248635976431672/flights-from-frederick-county) - [Flights to Frederick County ](https://www.expedia.com/Destinations-In-Frederick-County.d553248635976431672.Flight-Destinations) - [Flights from Winchester Regional ](https://www.expedia.com/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Richmond (RIC) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ric/wgo/richmond-to-winchester) - [Flights from Houston (IAH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/iah/wgo/houston-to-winchester) - 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[Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Tampa (TPA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tpa/wgo/tampa-to-winchester) - [Flights from Kansas City (MCI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mci/wgo/kansas-city-to-winchester) - [Flights to Winchester Regional ](https://www.expedia.com/Cheap-Flights-To-Winchester-Regional.d6033090.Travel-Guide-Flights) - [Flights from Minneapolis (MSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/msp/wgo/minneapolis-to-winchester) - [Flights from Cincinnati (CVG) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cvg/wgo/cincinnati-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Grand Rapids (GRR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/grr/wgo/grand-rapids-to-winchester) - [Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) - [Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) - [George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) - [Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction) - [Visit Old Town Winchester ](https://www.expedia.com/Winchester-Old-Town-Winchester.dx6164092) - [Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) - [Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Abram's Delight ](https://www.expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction) - [Nalls Farm Market ](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) - [Shenandoah University ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) - [Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) - [Car rentals near Old Town Winchester ](https://www.expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) - [Car rentals near Patsy Cline Historic House ](https://www.expedia.com/Car-Rentals-In-Patsy-Cline-Historic-House.d553248621532661841.Car-Rental-Guide) - [Car rentals near Nalls Farm Market ](https://www.expedia.com/Car-Rentals-In-Nalls-Farm-Market.d553248621532661846.Car-Rental-Guide) - [Car rentals near Shenandoah University ](https://www.expedia.com/Car-Rentals-In-Shenandoah-University.d6127311.Car-Rental-Guide) - [Van Car Rentals near Shenandoah University ](https://www.expedia.com/Van-Car-Rentals-In-Shenandoah-University.d6127311-tVan.Car-Rental-Guide-Class) - [Car rentals near Apple Blossom Mall ](https://www.expedia.com/Car-Rentals-In-Apple-Blossom-Mall.d6164018.Car-Rental-Guide) - [Car rentals near Winchester Medical Center ](https://www.expedia.com/Car-Rentals-In-Winchester-Medical-Center.d6164057.Car-Rental-Guide) - [Car rentals near College Park ](https://www.expedia.com/Car-Rentals-In-College-Park.d553248635975870482.Car-Rental-Guide) - [Car rental Winchester Airport (WGO) ](https://www.expedia.com/Car-Rentals-In-Winchester-Regional.d6033090.Car-Rental-Guide) \* Savings based on package bookings compared to the price of the same components booked separately. 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