We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

Winchester Hotels

  • Sort by:
  • Traveller Ranked
  • Lowest Price
  • Distance
TripAdvisor members only.
Login for exclusive access to hotel deals up to 40% off
Login to get best prices
Sponsored
#1 of 25 Hotels in Winchester by Best Value + Top Rated
US$82* /night
View Deal
TripAdvisor
US$82*
Expedia.com
US$82*
Hotwire.com
US$82*
View all 11 deals 
#1 of 25 Hotels in Winchester by Best Value + Top Rated
US$82* /night
View Deal
TripAdvisor
US$82*
Expedia.com
US$82*
Hotwire.com
US$82*
View all 11 deals 
#2 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$88*
US$68* /night
View Deal
TripAdvisor
US$68*
Booking.com
getaroom.com
US$88*
View all 12 deals 
#3 of 25 Hotels in Winchester by Best Value + Top Rated
US$94* /night
View Deal
TripAdvisor
US$94*
Country Inns
US$95*
Travelocity
US$95*
View all 11 deals 
#4 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$132*
US$120* /night
View Deal
TripAdvisor
US$120*
Booking.com
US$132*
Expedia.com
View all 9 deals 
#5 of 25 Hotels in Winchester by Best Value + Top Rated
US$70* /night
View Deal
TripAdvisor
US$70*
Expedia.com
US$70*
Red Roof
US$70*
View all 11 deals 
#6 of 25 Hotels in Winchester by Best Value + Top Rated
US$102* /night
View Deal
Booking.com
HolidayInn.com
US$102*
Travelocity
View all 10 deals 
#7 of 25 Hotels in Winchester by Best Value + Top Rated
US$112* /night
View Deal
TripAdvisor
US$111*
Travelocity
US$113*
Hotels.com
View all 10 deals 
#8 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$134*
US$112* /night
View Deal
TripAdvisor
US$112*
Hotwire.com
HotelQuickly
US$134*
View all 9 deals 
#9 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$127*
US$85* /night
View Deal
TripAdvisor
US$85*
Booking.com
HotelQuickly
US$127*
View all 11 deals 
#10 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$75*
US$64* /night
View Deal
Booking.com
US$75*
Hotwire.com
Travelocity
View all 9 deals 
#11 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$138*
US$132* /night
View Deal
TripAdvisor
US$132*
Hampton.com
getaroom.com
US$138*
View all 12 deals 
#12 of 25 Hotels in Winchester by Best Value + Top Rated
US$59* /night
View Deal
TripAdvisor
US$59*
Booking.com
Expedia.com
View all 9 deals 
#13 of 25 Hotels in Winchester by Best Value + Top Rated
US$96* /night
View Deal
TripAdvisor
US$96*
Hotels.com
HIExpress.com
US$97*
View all 10 deals 
#14 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$127*
US$108* /night
View Deal
TripAdvisor
US$108*
Expedia.com
Fairfield Inn
US$127*
View all 10 deals 
#15 of 25 Hotels in Winchester by Best Value + Top Rated
US$138* /night
View Deal
TripAdvisor
US$138*
Hampton.com
US$138*
Hotels.com
US$138*
View all 10 deals 
#16 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$139*
US$106* /night
View Deal
TripAdvisor
US$106*
Booking.com
HotelQuickly
US$139*
View all 10 deals 
#17 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$75*
US$64* /night
View Deal
TripAdvisor
US$64*
Booking.com
US$75*
Travelocity
View all 11 deals 
#18 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$135*
US$132* /night
View Deal
TripAdvisor
US$132*
Booking.com
US$135*
Orbitz.com
View all 12 deals 
#19 of 25 Hotels in Winchester by Best Value + Top Rated
US$115* /night
View Deal
TripAdvisor
US$115*
Booking.com
US$115*
Priceline
US$115*
View all 11 deals 
#20 of 25 Hotels in Winchester by Best Value + Top Rated
Top Deal
US$65*
US$63* /night
View Deal
TripAdvisor
US$63*
Hotels.com
Booking.com
US$65*
View all 9 deals 
#21 of 25 Hotels in Winchester by Best Value + Top Rated
Loading prices...
Hotwire.com
Hotels.com
Priceline
View all 9 deals 
#22 of 25 Hotels in Winchester by Best Value + Top Rated
#23 of 25 Hotels in Winchester by Best Value + Top Rated
No photo provided
#24 of 25 Hotels in Winchester by Best Value + Top Rated
Loading prices...
Expedia.com
Orbitz.com
Hotwire.com
View all 5 deals 
Loading prices...
Hotwire.com
*Prices are provided by our partners, and reflect average nightly room rates, including taxes and fees that are fixed, known to our partners, and due at time of booking. Please see our partners for more details.
Winchester Travel Forum Need specific advice visiting Winchester, Virginia? Visit the TripAdvisor Travel Forum for Winchester and ask our Destination Experts and the travel community.