Title: Old Town Winchester Vacation Packages & Trips 2025 from $340 | Expedia.ca [Hotels in Old Town Winchester](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Old Town Winchester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Old Town Winchester Price found within the past 48 hours. Click for updated prices. ![The Watergate Hotel](https://images.trvl-media.com/lodging/1000000/20000/13500/13429/4fa19413_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Watergate Hotel Northwest CA $639 per person Nov 2 - Nov 4 found 1 day ago Roundtrip flight included Toronto (YTZ) to Washington (WAS) 8.8/10 Excellent! (1,011 reviews) Pretty rough crowd. Lots of noise and parties. Parking at the hotel is $65 but you can park in the garage around the corner and under the hotel for $16. It’s kind of a sketchy walk from there to the hotel doors after dark though. It was interesting for the history of the place, but I would probably not stay here again. Reviewed on Oct 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-04/?FromAirport=YTZ&Destination=WAS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13429&paandie=true&dealMarker=6G4VshBxpt1VGdnGDnuoqnK9BVVXscZ7HvkhcHkwhIwVH2cAfHj7_ThQWc5Tj2N1) ![SIXTY DC](https://images.trvl-media.com/lodging/113000000/112940000/112935000/112934988/de097099_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### SIXTY DC Downtown Washington D.C. CA $650 per person Nov 4 - Nov 6 found 2 days ago Roundtrip flight included Toronto (YTZ) to Washington (WAS) 9.8/10 Exceptional! (55 reviews) Details. This place had high end features. Reviewed on Sep 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-04/2025-11-06/?FromAirport=YTZ&Destination=WAS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112934988&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnHzXBXJ5g2cWu6PTg1-vcirDFBPY3PkrWbdgc_im1a04) ![Willard InterContinental Washington by IHG](https://images.trvl-media.com/lodging/1000000/30000/23500/23405/e1160801_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Willard InterContinental Washington by IHG Downtown Washington D.C. CA $824 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YYZ) to Washington (WAS) 9.4/10 Exceptional! (1,008 reviews) Loved the traditional beautiful feel. Reviewed on Sep 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YYZ&Destination=WAS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23405&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnG_UHDfahnkKs0aTcJVMpz4bJI10Srt_QD-2e-CABVoo) ![Kimpton Hotel Monaco Washington DC by IHG](https://images.trvl-media.com/lodging/1000000/880000/871400/871361/2bb0833b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Monaco Washington DC by IHG Downtown Washington D.C. CA $877 per person Nov 5 - Nov 7 found 2 days ago Roundtrip flight included Toronto (YTZ) to Washington (DCA) 8.4/10 Very Good! (1,004 reviews) Comfortable, clean, very congenial staff -- great location, easy walking distance to the National Mall and to many places to eat indoors and outdoors. Reviewed on Sep 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-07/?FromAirport=YTZ&Destination=DCA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=871361&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnP-gtkre4YiDQsbSGzQG7zt7p66bBq1pLTrxjkczswVg) ![InterContinental Washington D.C. - The Wharf by IHG](https://images.trvl-media.com/lodging/17000000/16030000/16024200/16024166/a1ea6b4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Washington D.C. - The Wharf by IHG The Wharf CA $714 per person Nov 2 - Nov 4 found 1 day ago Roundtrip flight included Toronto (YTZ) to Washington (WAS) 9.4/10 Exceptional! (1,010 reviews) The property was beautiful. The staff was amazing and the area is so easy to get around plenty of dining and entertainment options. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-04/?FromAirport=YTZ&Destination=WAS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16024166&paandie=true&dealMarker=6G4VshBxpt1VGdnGDnuoqnK9BVVXscZ7HvkhcHkwhIwr8zvEQrNbIGjAYv21BOdW) ## Old Town Winchester Hotel Deals ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St, Winchester, VA Fully refundableReserve now, pay when you stay CA $177 CA $200 total Oct 9 - Oct 10 includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..." Reviewed on Sep 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F10%2F2025&endDate=10%2F10%2F2025&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6164092) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East, Winchester, VA Fully refundableReserve now, pay when you stay CA $151 CA $164 total Nov 2 - Nov 3 includes taxes & fees 9.2/10 Wonderful! (2,158 reviews) "Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually" Reviewed on Oct 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6164092) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive, Winchester, VA Fully refundableReserve now, pay when you stay CA $148 CA $168 total Oct 13 - Oct 14 includes taxes & fees 9/10 Wonderful! (1,014 reviews) "We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you!" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6164092) [See all 366 properties in Old Town Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=6164092) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does an Old Town Winchester vacation package cost? > Our Old Town Winchester vacation packages, which begin from just CA $639, are the best way to save. All you have to do is choose your preferred hotels, flights and rental car to create your perfect getaway. ### How do I get a cheap travel package to Old Town Winchester? > Our Old Town Winchester vacation packages offer plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into a handy package. But low prices are only the start of your next epic adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotels around the world to pick from. Whatever your budget or style, there's a package that's perfect for you. ### Where should I stay in Old Town Winchester? > A vacation in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Center and Museum of the Shenandoah Valley. Spend your evenings near these tourist attractions and make sightseeing a breeze. ### What are the top hotels in Old Town Winchester? > Whether you plan to stay for a night or a week in Old Town Winchester, you'll get a wonderful night's rest at [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information). This option is a favorite with lots of travelers. ### How far in advance should I book my Old Town Winchester vacation? > You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester vacation nice and early. Airlines typically advertise tickets anywhere up to 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so there's never a bad time to book your dream vacation! ### What does an Expedia Old Town Winchester travel package include? > Flights, hotels and car rentals — we connect you to all the best deals. All you'll have to do is decide on your favorite combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to craft an amazing Old Town Winchester getaway. ### What should I know before booking an Old Town Winchester travel package? > We already have low prices. However, you'll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a terrific range of choice. ### Can I choose my airline with an Old Town Winchester Expedia vacation package? > With a vacation package, you're in charge. Whether you're looking to fly to Old Town Winchester in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world. ### If I'm not able to travel, can I cancel my Old Town Winchester vacation package? > Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, browse our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105). We're here to help you every step of the way. ### Discover the most popular places to visit in Old Town Winchester #### 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.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.