Deals on vacations and trips to Old Town Winchester
Old Town Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
citizenM Washington DC Georgetown
Northwest
Price was $702, price is now $465 per person
$465
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was $1,244, price is now $683 per person
$683
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Price was $1,392, price is now $928 per person
$928
per person
Jan 24 - Jan 30
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
The Potomac Hotel, Autograph Collection
Southwest
Price was $1,389, price is now $926 per person
$926
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Save 100% on your flight
Price was $797, price is now $543 per person
$543
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Top Old Town Winchester hotels deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$130 nightly
The price is $148 total per night
$148 total
Nov 8 - Nov 9
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and concierge services.
Pool
Spa
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $77 total per night
$77 total
Dec 1 - Dec 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock assistance.
Pet friendly
Parking included
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $92 total per night
$92 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $89 total per night
$89 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $84 total per night
$84 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $121 total per night
$121 total
Nov 4 - Nov 5
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Old Town Winchester
View all propertiesLowest 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.
Stay near popular Old Town Winchester attractions
Frequently asked questions
Photos of local treasures
Browse Old Town Winchester vacation photos for more inspiration
