Title: Visit Winchester: 2026 Travel Guide for Winchester, Virginia | Expedia.com

[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)[Winchester Vacation Packages](https://expedia.com/Winchester.d6056879.Destination-Travel-Guides)

# Winchester, VA

## Travel Guide

![Winchester](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Winchester](https://images.trvl-media.com/place/6056879/dd3561a1-54d7-46cf-9e70-15a3b654b5eb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Winchester](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Winchester](https://images.trvl-media.com/place/6056879/3acc501a-a330-4063-b538-b2368ef6a4c5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Winchester

Where to stay

Things to do

### Where to stay in Winchester

![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.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.com/Winchester-Old-Town-Winchester.dx6164092)

![Buildings and streets in the historic part of the ancient city of Winchester in Virginia.](https://images.trvl-media.com/place/918789051029594112/06c2fe17-e2c5-4e1c-941c-f181c2f40c91.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.com/Winchester-Winchester-Historic-District.dx918789051029594112)

[See our Where To Stay guide](https://expedia.com/Winchester.dx6056879.Where-To-Stay?rfrr=TG.LP.Dest.Neighborhoods)

- Winchester Hotel Deals
- Vacation Rentals in Winchester

![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

$91 nightly

$99 total

Apr 12 - Apr 13

Total with taxes and fees

Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...

9/10 Wonderful! (1,002 reviews)

Great staff, rooms are nice love going there they treat me like a queen.

Reviewed on Apr 5, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true&regionId=6056879)

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

$110 nightly

$119 total

Apr 6 - Apr 7

Total with taxes and fees

Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

9.2/10 Wonderful! (2,272 reviews)

Parking was convenient. I didn’t get up in time for the breakfast.

Reviewed on Apr 4, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true&regionId=6056879)

![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sleep Inn & Suites Winchester near University

140 Costello Dr Winchester VA

$80 nightly

$87 total

Apr 26 - Apr 27

Total with taxes and fees

Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

7.8/10 Good! (1,001 reviews)

I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature

Reviewed on Mar 26, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=892882&PinnedHotelID=892882&HadPinnedHotel=true&regionId=6056879)

[See all 2,079 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&regionId=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.

![Dreamtime - Modern A-frame Cabin w/ Hot tub](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/9fcb6e62_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Dreamtime - Modern A-frame Cabin w/ Hot tub

 Berkeley Springs WV

Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...

10/10 Exceptional! (57 reviews)

The house was beautiful and well taken care of. We had everything we needed to just hold up cozy in the house. The hot tub was a great ammenity.

Reviewed on Jan 23, 2026

[](https://expedia.com/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information)

![Cozy Bear Cottage! Hot Tub! Warm toasty fireplace!](https://images.trvl-media.com/lodging/43000000/42620000/42617400/42617315/32780271_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cozy Bear Cottage! Hot Tub! Warm toasty fireplace!

 Luray VA

Stay at this cabin in Luray. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Luray Caverns and Dukes of Hazzard Museum are located ...

10/10 Exceptional! (92 reviews)

Didn't use the fireplace,but the kitchen was wonderful,had everything we needed,loved the set up,it was very inviting,the telephone was really interesting!!All the decor on the walls added made the area more interesting,thank you

Reviewed on Mar 25, 2026

[](https://expedia.com/Luray-Hotels-A-Cozy-Bear-Cottage-Clean-And-Secluded.h42617315.Hotel-Information)

!["Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

 Rileyville VA

Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...

10/10 Exceptional! (351 reviews)

Everything was absolutely amazing! Thank you!

Reviewed on Apr 3, 2026

[](https://expedia.com/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information)

[See all properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6056879&sort=VACATION_RENTAL)

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.

## Check Winchester hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=2026-04-05&endDate=2026-04-06)[Apr 5 - Apr 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=2026-04-05&endDate=2026-04-06)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=2026-04-06&endDate=2026-04-07)[Apr 6 - Apr 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=2026-04-06&endDate=2026-04-07)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6056879&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)

### Popular places to visit

![Museum of the Shenandoah Valley](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 top-notch restaurants or charming coffeehouses 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)

#### Shenandoah University

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants. 

[](https://expedia.com/Shenandoah-University-Winchester.d6127311.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)

#### Apple Blossom Mall

You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants. 

[](https://expedia.com/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction)

#### Shenandoah Valley Discovery Museum

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants. 

[](https://expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction)

## Cities near Winchester

![Trees - Bear Church Rock Trail, Shenandoah National Park, Virginia](https://images.trvl-media.com/place/7312/1e808d74-e702-47a6-a388-ce77751dfd04.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Front Royal

![Middletown](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Middletown

![Sunrise in Shenandoah National Park](https://images.trvl-media.com/place/12076/44755a2b-1105-46ba-bd69-9edb9351f673.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Stephens City

![Aerial View of Train Yard Waiting for Thomas](https://images.trvl-media.com/place/55195/f2bb0afc-1224-4dd7-9a80-eb713e0793b8.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Strasburg

### Other places like Winchester

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- [Flights from Columbus (CMH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cmh/wgo/columbus-to-winchester)
- [Flights from Indianapolis (IND) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ind/wgo/indianapolis-to-winchester)
- [Flights from St. Louis (STL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/stl/wgo/st-louis-to-winchester)
- [Flights from Los Angeles (LAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/lax/wgo/los-angeles-to-winchester)
- [Flights from Savannah (SAV) to Winchester (WGO) ](https://www.expedia.com/lp/flights/sav/wgo/savannah-to-winchester)
- [Flights from San Diego (SAN) to Winchester (WGO) ](https://www.expedia.com/lp/flights/san/wgo/san-diego-to-winchester)
- [Flights from Myrtle Beach (MYR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/myr/wgo/myrtle-beach-to-winchester)
- [Flights from Detroit (DTW) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dtw/wgo/detroit-to-winchester)
- [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)

- [Visit Old Town Winchester ](https://www.expedia.com/Winchester-Old-Town-Winchester.dx6164092)
- [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)
- [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 ValleyHealth 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)

- Cities near Winchester
- Places of interest

[Front Royal](https://expedia.com/Front-Royal.dx7312)[Middletown](https://expedia.com/Middletown.dx12013)[Stephens City](https://expedia.com/Stephens-City.dx12076)[Strasburg](https://expedia.com/Strasburg.dx55195)[Berkeley Springs](https://expedia.com/Berkeley-Springs.dx55584)[Berryville](https://expedia.com/Berryville.dx184082)[Boyce](https://expedia.com/Boyce.dx184084)[White Post](https://expedia.com/White-Post.dx184119)[Hedgesville](https://expedia.com/Hedgesville.dx184160)[Gore](https://expedia.com/Gore.dx3000460015)[Star Tannery](https://expedia.com/Star-Tannery.dx3000460674)[Gerrardstown](https://expedia.com/Gerrardstown.dx3000461232)[Cross Junction](https://expedia.com/Cross-Junction.dx553248635975978078)

- [Shenandoah University ](https://expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction)
- [ValleyHealth Winchester Medical Center ](https://expedia.com/ValleyHealth-Winchester-Medical-Center-Winchester.d6164057.Vacation-Attraction)
- [Museum of the Shenandoah Valley ](https://expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction)
- [Apple Blossom Mall ](https://expedia.com/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction)
- [Shenandoah Valley Discovery Museum ](https://expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction)
- [Patsy Cline Historic House ](https://expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction)
- [Rock Harbor Golf Course ](https://expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction)
- [Bright Box Theater ](https://expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction)
- [Jim Barnett Park ](https://expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction)
- [Mt Hebron Cemetery ](https://expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction)
- [Stonewall Jackson's Headquarters ](https://expedia.com/Stonewall-Jacksons-Headquarters-Winchester-Historic-District.d6164032.Vacation-Attraction)
- [Winchester Little Theater ](https://expedia.com/Winchester-Little-Theater-Winchester-Historic-District.d6164047.Vacation-Attraction)
- [The Kernstown Battlefield ](https://expedia.com/The-Kernstown-Battlefield-Winchester.d553248621561864837.Vacation-Attraction)
- [Handley Regional Library ](https://expedia.com/Handley-Regional-Library-Old-Town-Winchester.d6164024.Vacation-Attraction)
- [Abram's Delight ](https://expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction)
- [Rocking S Ranch ](https://expedia.com/Rocking-S-Ranch-Winchester.d553248621587527633.Vacation-Attraction)
- [George Washington's Office ](https://expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction)

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