Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Feb 14 - Feb 15
Tomorrow
Feb 15 - Feb 16
Next weekend
Feb 20 - Feb 22
In two weeks
Feb 27 - Mar 1

Where to stay in Winchester?

Exterior
Comfort Inn & Suites Winchester
Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,099 reviews)
  • cleanliness
    Modern Winchester hotel with free breakfast, fitness center, and Wi-Fi access.
The price is $98
$106 total
includes taxes & fees
Feb 22 - Feb 23
Comfort Inn & Suites Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into a convenient stay by Winchester's historic sites with relaxing indoor pool.
The price is $78
$88 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,001 reviews)
The price is $83
$91 total
includes taxes & fees
Feb 22 - Feb 23
Country Inn & Suites by Radisson, Winchester, VA
Lobby
Spark by Hilton Winchester
Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Enjoy a peaceful stay with easy highway access and friendly service at this property.
The price is $82
$93 total
includes taxes & fees
Feb 22 - Feb 23
Spark by Hilton Winchester
Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free cribs/infant beds
Quality Inn Winchester
Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
The price is $84
$92 total
includes taxes & fees
Feb 20 - Feb 21
Quality Inn Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,444 reviews)
  • cleanliness
    Cozy stay with modern comforts near local attractions and shopping centers.
The price is $86
$93 total
includes taxes & fees
Feb 22 - Feb 23
Microtel Inn & Suites by Wyndham Winchester
Dining
Wayside Inn
Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (422 reviews)
The price is $80
$98 total
includes taxes & fees
Feb 16 - Feb 17
Wayside Inn
Exterior
SpringHill Suites by Marriott Winchester
SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (810 reviews)
  • cleanliness
    Modern Winchester retreat with indoor pool and 24-hour fitness center access.
The price is $107
$117 total
includes taxes & fees
Feb 22 - Feb 23
SpringHill Suites by Marriott Winchester
Lobby
Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    A relaxing Shenandoah Valley retreat with onsite dining and fitness amenities.
The price is $76
$84 total
includes taxes & fees
Mar 2 - Mar 3
Ramada by Wyndham Strasburg/Shenandoah Valley
Exterior
Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very Good, (819 reviews)
The price is $84
$91 total
includes taxes & fees
Feb 18 - Feb 19
Holiday Inn Express Winchester South-Stephens City by IHG
Indoor pool
Hampton Inn Front Royal
Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    A welcoming retreat near Shenandoah National Park with indoor pool and free perks.
The price is $98
$109 total
includes taxes & fees
Feb 22 - Feb 23
Hampton Inn Front Royal
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Modern retreat with golf course and indoor pool near Shenandoah National Park.
The price is $98
$108 total
includes taxes & fees
Feb 22 - Feb 23
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,266 reviews)
  • cleanliness
    Comfortable beds await at this Winchester gem with a refreshing indoor pool.
The price is $100
$109 total
includes taxes & fees
Feb 16 - Feb 17
La Quinta Inn & Suites by Wyndham Winchester
Lobby lounge
Fairfield Inn & Suites Strasburg Shenandoah Valley
Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,000 reviews)
The price is $113
$126 total
includes taxes & fees
Feb 22 - Feb 23
Fairfield Inn & Suites Strasburg Shenandoah Valley
Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Relax in a Georgian spa hotel near Winchester's Civil War Museum and theaters.
The price is $122
$138 total
includes taxes & fees
Feb 22 - Feb 23
The George Washington Hotel, A Wyndham Grand Hotel
Free daily continental breakfast
Quality Inn Stephens City - Winchester South
Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very Good, (637 reviews)
  • cleanliness
    Quiet stay near Appleland Sports Center with fitness center and outdoor pool.
The price is $74
$80 total
includes taxes & fees
Mar 2 - Mar 3
Quality Inn Stephens City - Winchester South
Lobby
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Peaceful retreat near Shenandoah National Park with complimentary breakfast service.
The price is $62
$69 total
includes taxes & fees
Feb 16 - Feb 17
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Porch
Relax Inn Motel
Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very Good, (260 reviews)
  • cleanliness
    Unwind 10 minutes from Shenandoah National Park with complimentary parking.
The price is $62
$69 total
includes taxes & fees
Feb 16 - Feb 17
Relax Inn Motel
Lobby sitting area
Motel 6 Winchester, VA
Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Peaceful Winchester getaway with easy access to the Apple Blossom Mall and battlefield.
The price is $68
$77 total
includes taxes & fees
Feb 16 - Feb 17
Motel 6 Winchester, VA
Interior entrance
Gateway Inn
Gateway Inn
2.0 star property
Front Royal
5.0 out of 10, (10 reviews)
  • cleanliness
    Convenient Front Royal lodging near Shenandoah National Park and river.
The price is $70
$78 total
includes taxes & fees
Feb 16 - Feb 17
Gateway Inn
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.
View all properties

Get last-minute hotel deals in Winchester and save more

Sign in to unlock great savings.
Showing deals for:Feb 20 - Feb 22
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
The price is $82
per night
$185 total
includes taxes & fees
MOD
Sign in for extra savings
Holiday Inn Winchester Se-Historic Gateway by IHG

Check out pet-friendly hotels in Winchester

Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
The price is $82
$93 total
includes taxes & fees
Feb 22 - Feb 23
Spark by Hilton Winchester
View all properties

You may also like hotels with pools in Winchester

Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1000)
The price is $78
$88 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Winchester Se-Historic Gateway by IHG
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.
View all properties

When is the best time to visit Winchester?

Our prices for hotels in Winchester are cheapest in February
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
View properties in February
Currently viewing crowd sizes and weather for February.
Typical weather for Winchester
February
High 6°C / low -3°C. Snow likely.
View properties in February
6°
ac_unit
February, no crowd data, average high temperature 6 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
11°
weather_partly_sunny
March, no crowd data, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
1°
17°
weather_sun
April, no crowd data, average high temperature 17 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
6°
22°
weather_sun
May, no crowd data, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
27°
weather_sun
June, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
16°
30°
weather_sun
July, no crowd data, average high temperature 30 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
weather_sun
August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
25°
weather_sun
September, no crowd data, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
18°
weather_sun
October, no crowd data, average high temperature 18 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
9°
11°
weather_sun
November, no crowd data, average high temperature 11 degrees Celsius, average low temperature 2 degrees Celsius. Sunny most days.
2°
7°
weather_partly_sunny
December, no crowd data, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
4°
ac_unit
January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
-4°
Monthly weather averages (˚C)

Top neighborhoods in Winchester

The Courthouse in Winchester, Virginia.

Old Town Winchester

Winchester's Old Town Winchester neighborhood is known for its restaurants and bars, and entices visitors with attractions including Bright Box Theater and Shenandoah Valley Discovery Museum.

A nice 3 block outdoor downtown shopping area with dining and bars also.
Photo by Fernando Begay
Open Photo by Fernando Begay

Winchester Historic District

Winchester's Winchester Historic District neighborhood is home to attractions such as Bright Box Theater and Shenandoah Valley Discovery Museum.

Top landmarks in Winchester

Gardens at Glen Burnie House.
Photo by Tina McClelland
Open Photo by Tina McClelland

Museum of the Shenandoah Valley

4.5/5 (47 reviews)
The MSV showcases the Valley's rich heritage through art galleries and the historic Glen Burnie House. Wander through meticulously designed gardens with outdoor sculptures while following scenic trails.
See properties
Jim Barnett park
Photo by Mominator Madness
Open Photo by Mominator Madness

Jim Barnett Park

4.0/5 (31 reviews)
Jim Barnett Park spans 170 acres with trails, sports fields, and a fishing lake for outdoor enthusiasts. Grab a picnic and use the shelters with grills for a relaxing day under mature trees.
See properties

Winchester and related destinations

Wander through America's oldest pedestrian mall, where historic buildings house quirky shops and restaurants that locals fiercely defend as the valley's best. The Museum of the Shenandoah Valley tells stories through art and gardens that change dramatically with the seasons. Civil War buffs can explore Stonewall Jackson's Headquarters, where the general's personal items remain eerily untouched. Patsy Cline's modest historic house offers an intimate glimpse into the country legend's early life before Nashville fame. After dark, Bright Box Theater fills with laughter and live music in a space that feels both sophisticated and warmly familiar. Kids can touch everything at the hands-on Shenandoah Valley Discovery Museum, a welcome relief for parents tired of saying 'don't touch that.'

See all hotels in Winchester

Check out reviews of Winchester hotels guests love

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

10/10 Excellent
"Friendly staff Clean room Good breakfast Nice place to stay "
Lisa 1-night trip
Posted 4 days ago
Holiday Inn Express Charles Town by IHG

Frequently asked questions

What hotels do travelers like in Winchester?
SpringHill Suites by Marriott Winchester, The George Washington Hotel, A Wyndham Grand Hotel and Quality Inn Winchester are all properties that our guests really like.
Can I book a refundable hotel in Winchester?
If you're looking for the flexibility to change your travel plans to Winchester, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Winchester if I'm looking for a budget-friendly accommodation?
A few inexpensive options worth considering are Quality Inn Winchester, Microtel Inn & Suites by Wyndham Winchester and Hampton Inn Winchester N/Conference Center, VA.
Where can I stay in Winchester if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, review our selection of 14 vacation homes. In addition, you can choose from 26 apartments.
What will the weather in Winchester be like during my visit?
July and August are typically the warmest months in Winchester when the average temp is 72°F. January and February are the coldest months when the average temperature is 36°F. May and September are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.