Title: 10 TOP Things to Do in Winchester December 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) # What to do in Winchester, VA ## Activities, attractions and tours ## Visit Winchester Types of activities Where to stay [Winchester travel guide](https://expedia.ca/Winchester.dx6056879) ![Winchester](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg) ## Winchester Attractions Let Expedia help you experience the best that Winchester has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes. #### Activities and Tours Winchester is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Winchester to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind. If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights. #### Winchester Attractions Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Winchester. Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Winchester attractions ensure that you’ll have a successful trip, whatever the season. --- - ![find price illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__find_price.svg) ### Explore activities Explore thousands of experiences from activities and attractions to day tours and transfer. - ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Book with ease Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities. - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself Members save % or more when you book activities. --- ## Recommended things to do in Winchester | Number of things to do | 1 | | ------------------------------- | --------------------------------------------------------------------------------------------------------------------------------------- | | Cheapest thing to do on Expedia | [Shenandoah Tour: Self-Guided Drive](/things-to-do/shenandoah-national-park-self-guided-driving-tour.a5064646.activity-details): CA $22 | | Top 5 things to do | [Shenandoah Tour: Self-Guided Drive](/things-to-do/shenandoah-national-park-self-guided-driving-tour.a5064646.activity-details) | | Half-day tours | | | With kids | | ## What to do in Winchester --- ### Explore areas of Winchester ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Town Winchester Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area. [](https://expedia.ca/Winchester-Old-Town-Winchester.dx6164092) ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Winchester Historic District While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum. [](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112) --- Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. --- ## Day trip destinations from Winchester ![Photo by Stephanie Sutton](https://mediaim.expedia.com/destination/2/0f9fdd213769c5b9ea606378c29239ea.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### White Post ## Frequently asked questions ### Is Winchester worth visiting? ### How do I spend a day in Winchester? ### What is the top tourist attraction in Winchester? ### Is three days enough to stay in Winchester? ### Is Winchester a walkable city? ### What are some activities to do in Winchester with kids? ### What to do in Winchester for adults? ### Are there free things to do in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Other - [3 Star Hotels in Old Town Winchester ](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Apartments in Boyce ](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce ](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Boyce ](https://www.expedia.ca/Boyce-Hotels-Boutique-Hotel.0-0-d184084-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Boyce Hotels ](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [Motels in Boyce ](https://www.expedia.ca/Boyce-Motels.d184084-aaMotels.Travel-Guide-Accommodation) - [Hotels near Bright Box Theater ](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [Motels in Brucetown ](https://www.expedia.ca/Brucetown-Motels.d3000355042-aaMotels.Travel-Guide-Accommodation) - [Cheap Hotels in Clear Brook ](https://www.expedia.ca/Clear-Brook-Hotels-Cheap-Hotels.0-0-d553248635975870250-tCheapHotels.Travel-Guide-Filter-Hotels) - [Clear Brook Hotels ](https://www.expedia.ca/Clear-Brook-Hotels.d553248635975870250.Travel-Guide-Hotels) - [B&B in College Park ](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Vacation Homes in College Park ](https://www.expedia.ca/College-Park-Private-Vacation-Homes.d553248635975870482-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels near Dinosaur Land ](https://www.expedia.ca/Dinosaur-Land-Hotels.0-l553248621532661835-0.Travel-Guide-Filter-Hotels) - [B&B in Frederick County ](https://www.expedia.ca/Frederick-County-Bed-And-Breakfast.d553248635976431672-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Frederick County ](https://www.expedia.ca/Frederick-County-Cottages.d553248635976431672-aaCottages.Travel-Guide-Accommodation) - [Gainesboro Hotels ](https://www.expedia.ca/Gainesboro-Hotels.d553248635976006643.Travel-Guide-Hotels) - [Hotels near George Washington's Office ](https://www.expedia.ca/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels) - [B&B in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Bed-And-Breakfast.d553248635975872368-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Cottages.d553248635975872368-aaCottages.Travel-Guide-Accommodation) - [Villas in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Villas.d553248635975872368-aaVillas.Travel-Guide-Accommodation) - [Luxury Hotels in Kernstown ](https://www.expedia.ca/Kernstown-Hotels-Luxury-Hotel.0-0-d553248635975850140-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Kernstown Hotels ](https://www.expedia.ca/Kernstown-Hotels.d553248635975850140.Travel-Guide-Hotels) - [Hotels near Mt Hebron Cemetery ](https://www.expedia.ca/Mt-Hebron-Cemetery-Hotels.0-l553248621532661845-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Cheap-Hotels.0-n6164092-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Balconies.0-n6164092-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Breakfast.0-n6164092-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Parking.0-n6164092-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Smoking-Rooms.0-n6164092-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Luxury-Hotel.0-n6164092-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Pet-Friendly-Hotel.0-n6164092-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Old Town Winchester Hotels ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House ](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Harbor Golf Course ](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [B&B in Stephens City ](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Pet-Friendly-Hotel.0-0-d12076-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Stephens City Hotels ](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels) - [Hotels near Valerie Hill Winery ](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels) - [White Post Hotels ](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau ](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center ](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Flights to Boyce ](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights from Winchester Regional ](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Clear Brook ](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center ](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Things to do in Alexandria ](https://www.expedia.ca/Things-To-Do-In-Alexandria.d5980.Travel-Guide-Activities) - [Things to do in Amissville ](https://www.expedia.ca/Things-To-Do-In-Amissville.d3000355000.Travel-Guide-Activities) - [Things to do in Annandale ](https://www.expedia.ca/Things-To-Do-In-Annandale.d74038.Travel-Guide-Activities) - [Things to do in Arlington ](https://www.expedia.ca/Things-To-Do-In-Arlington.d6236.Travel-Guide-Activities) - [Things to do in Barboursville ](https://www.expedia.ca/Things-To-Do-In-Barboursville.d6349287.Travel-Guide-Activities) - [Things to do in Blue Ridge ](https://www.expedia.ca/Things-To-Do-In-Blue-Ridge.d553248635976006713.Travel-Guide-Activities) - [Things to do in Bluemont ](https://www.expedia.ca/Things-To-Do-In-Bluemont.d6348602.Travel-Guide-Activities) - [Things to do in Central ](https://www.expedia.ca/Things-To-Do-In-Central.d553248635976006913.Travel-Guide-Activities) - [Things to do in Centreville ](https://www.expedia.ca/Things-To-Do-In-Centreville.d603264.Travel-Guide-Activities) - [Things to do in Chantilly ](https://www.expedia.ca/Things-To-Do-In-Chantilly.d8638.Travel-Guide-Activities) - [Things to do in Falls Church ](https://www.expedia.ca/Things-To-Do-In-Falls-Church.d8077.Travel-Guide-Activities) - [Things to do in Fort Valley ](https://www.expedia.ca/Things-To-Do-In-Fort-Valley.d6353682.Travel-Guide-Activities) - [Things to do in Fredericksburg ](https://www.expedia.ca/Things-To-Do-In-Fredericksburg.d8145.Travel-Guide-Activities) - [Things to do in Greenwood ](https://www.expedia.ca/Things-To-Do-In-Greenwood.d6353665.Travel-Guide-Activities) - [Things to do in Harrisonburg ](https://www.expedia.ca/Things-To-Do-In-Harrisonburg.d6056902.Travel-Guide-Activities) - [Things to do in Haymarket ](https://www.expedia.ca/Things-To-Do-In-Haymarket.d6155337.Travel-Guide-Activities) - [Things to do in Hillsboro ](https://www.expedia.ca/Things-To-Do-In-Hillsboro.d3000460046.Travel-Guide-Activities) - [Things to do in Leesburg ](https://www.expedia.ca/Things-To-Do-In-Leesburg.d8575.Travel-Guide-Activities) - [Things to do in Manassas ](https://www.expedia.ca/Things-To-Do-In-Manassas.d8779.Travel-Guide-Activities) - [Things to do in McLean ](https://www.expedia.ca/Things-To-Do-In-McLean.d8773.Travel-Guide-Activities) - [Things to do in Middleburg ](https://www.expedia.ca/Things-To-Do-In-Middleburg.d55837.Travel-Guide-Activities) - [Things to do in Northern Virginia ](https://www.expedia.ca/Things-To-Do-In-Northern-Virginia.d6057018.Travel-Guide-Activities) - [Things to do in Reston ](https://www.expedia.ca/Things-To-Do-In-Reston.d10437.Travel-Guide-Activities) - [Things to do in Round Hill ](https://www.expedia.ca/Things-To-Do-In-Round-Hill.d3000460647.Travel-Guide-Activities) - [Things to do in Scottsville ](https://www.expedia.ca/Things-To-Do-In-Scottsville.d184107.Travel-Guide-Activities) - [Things to do in Stanley ](https://www.expedia.ca/Things-To-Do-In-Stanley.d184111.Travel-Guide-Activities) - [Things to do in Sterling ](https://www.expedia.ca/Things-To-Do-In-Sterling.d9843.Travel-Guide-Activities) - [Things to do in Tysons ](https://www.expedia.ca/Things-To-Do-In-Tysons.d553248629256461015.Travel-Guide-Activities) - [Things to do in Waynesboro ](https://www.expedia.ca/Things-To-Do-In-Waynesboro.d6733.Travel-Guide-Activities) - [Things to do in Woodbridge ](https://www.expedia.ca/Things-To-Do-In-Woodbridge.d10364.Travel-Guide-Activities) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app