Title: Winchester Vacation Packages & Trips 2026 from CA $765 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975872164.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975872164.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975872164.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) # 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 #### Your Winchester Vacation History, cuisine, art and more … There's so much to discover with a Winchester vacation package. And with the ability to customize your city break, it's guaranteed to be one you won't forget. Eager to start exploring your surroundings? [Fair Hill State Natural Resources Management Area](https://www.expedia.ca/Fair-Hill-State-Natural-Resources-Management-Area-Elkton.d6187511.Vacation-Attraction), [Patriots Glen Golf Club](https://www.expedia.ca/Patriots-Glen-Golf-Club-Elkton.d553248621532663262.Vacation-Attraction) and [East Meadow Park](https://www.expedia.ca/East-Meadow-Park-Elkton.d553248621532663261.Vacation-Attraction) are among the leading places to visit during your trip to Winchester. Your dream Winchester vacation is a couple of clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored to suit your style. ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Hotel Laurel](https://images.trvl-media.com/lodging/1000000/10000/4500/4480/2ba6a934_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Hotel Laurel West Laurel CA $765 per person Mar 17 - Mar 21 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (1,002 reviews) The room was clean, staff was helpful and nice. Reviewed on Feb 8, 2026 ![Crowne Plaza College Park - Washington DC by IHG](https://images.trvl-media.com/lodging/1000000/30000/24400/24323/d62e82a1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crowne Plaza College Park - Washington DC by IHG CA $782 per person Mar 17 - Mar 21 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 8.4/10 Very Good! (2,116 reviews) Everything was as expected. Hotel was quiet, the room was clean and the breakfast buffet was very good. Wish the in lobby bar/resturant was open later than 10pm after a long day of travel. No big deal, thank you. Reviewed on Feb 8, 2026 ![Lord Baltimore Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16091/99db7240_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lord Baltimore Hotel Downtown Baltimore CA $1,057 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (2,362 reviews) The entire floor smelled like weed. From what others told me their floors smelled like weed too. Also is a haunted hotel. So if you’re cool with ghosts and the smell of weed, it’s otherwise clean and the staff were very nice. Reviewed on Feb 4, 2026 ![The Westin Baltimore Washington Airport - BWI](https://images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/13f895c7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Baltimore Washington Airport - BWI CA $921 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Baltimore (BWI) 8.8/10 Excellent! (1,082 reviews) Clean room, nice staff and great amenities Reviewed on Feb 5, 2026 ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Newark - Wilmington 65 Geoffrey Dr Newark DE Fully refundableReserve now, pay when you stay CA $82 CA $91 total Feb 20 - Feb 21 includes taxes & fees 5.2/10 (1,007 reviews) Nice staff, room quiet Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F02%2F2026&endDate=21%2F02%2F2026&selected=25008&PinnedHotelID=25008&HadPinnedHotel=true®ionId=553248635975872164) ![Sheraton Suites Wilmington Downtown](https://images.trvl-media.com/lodging/1000000/10000/4700/4693/72ec9ef5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Suites Wilmington Downtown 422 Delaware Ave Wilmington DE Fully refundableReserve now, pay when you stay CA $174 CA $191 total Feb 13 - Feb 14 includes taxes & fees 8.2/10 Very Good! (1,004 reviews) Always the best place with early check in. Clean and cozy with super awesome customer service. Reviewed on Jan 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F02%2F2026&endDate=14%2F02%2F2026&selected=4693&PinnedHotelID=4693&HadPinnedHotel=true®ionId=553248635975872164) ![Great Wolf Lodge Perryville](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/f3cb543b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Perryville 1240 Chesapeke Overlook Parkway Perryville MD Fully refundable CA $272 CA $305 total Feb 11 - Feb 12 includes taxes & fees 8.6/10 Excellent! (172 reviews) We really has a good time for our overnight stay. We going back soon Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=103097849&PinnedHotelID=103097849&HadPinnedHotel=true®ionId=553248635975872164) [See all 641 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®ionId=553248635975872164) 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) ### Discover the most popular places to visit in Winchester #### Elkton Indoor Tennis Catch an event at Elkton Indoor Tennis during your trip to Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.ca/Elkton-Indoor-Tennis-Elkton.d553248621532663263.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app