Title: Winchester Vacation Packages & Trips 2025/2026 from CA $574 | 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. ![Hotel Ulysses, a Member of Design Hotels](https://images.trvl-media.com/lodging/76000000/75800000/75794200/75794138/47fe035f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Ulysses, a Member of Design Hotels Mount Vernon CA $574 per person Jan 15 - Jan 18 just found Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 9.2/10 Wonderful! (966 reviews) Arrived late at the hotel on a cold and rainy evening, to find the room with the AC blasting at 68F. You can't control the heating because is centralized. I texted the number they gave me at the reception but there was no response or follow-up. So I had to let the room slowly heat-up (by morning it was already 72). One big advantadge is that the room is tiny. Extremely tiny. The positive side is I guess it does warm up faster as a result. My room was at the higher floor so the (warm) water pressure was very low - in case you consider warming up with a hot shower. And even after a few good minutes it was still lukewarm rather than hot - I wasn't able to get hot water. Parking was OK. Used the public parking across the street, for much cheaper rates than the valet at the hotel. The only inconvenience is extending the parking time, it seems that you can't do it online, you have to physically go back to the lot. Everything else, it was great. Also the room and the bathroom were very clean, I truly appreciate that! Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=75794138&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4hKdliYFOiMIoPPLr2mk8qCGsrkP67KVVykuyWv-5e22) ![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 $629 per person Jan 15 - Jan 18 just found Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (2,279 reviews) For the price, the rooms are really old and there’s a lot of water damage with the wallpaper around the ceiling area. You can tell there’s not a lot of ventilation in the rooms. Would be really great if they switched out to handheld showerheads so us ladies could wash our private bits I think those showerheads are from the 80s. That would really make the property look a little bit more upgraded for the price. The staff were very lovely. That’s the saving factor of this property besides location since we are across the street from our concert venue. They also always have cold water for free with cups in the lobby. However, I did get charged extra for valet so now I’m trying to sort that out. And the elevators were a nightmare. Everyone came back in the evening around the same time and there was not only the concert but also two other events in the hotel so a lot of people needing to get upstairs at once. They need to have those other elevators fixed up and running two of them were out of service. Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16091&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4lCqc2WhSeeeW49RDs7lXfdNmxCBvKQyU39FxPJ4N2l-) ![Kimpton Hotel Monaco Baltimore Inner Harbor by IHG](https://images.trvl-media.com/lodging/3000000/2670000/2663700/2663612/6f643942_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Monaco Baltimore Inner Harbor by IHG Downtown Baltimore CA $627 per person Jan 15 - Jan 18 just found Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 8.8/10 Excellent! (157 reviews) The service and room Reviewed on Oct 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2663612&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4lCqc2WhSeeeW49RDs7lXff6UgUE-H4lR_eu6e84J6Ox) ![Sonesta Hotel Baltimore Inner Harbor](https://images.trvl-media.com/lodging/17000000/16530000/16526500/16526456/debe7b21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sonesta Hotel Baltimore Inner Harbor Downtown Baltimore CA $609 per person Jan 15 - Jan 18 just found Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (940 reviews) Great and friendly staff. Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16526456&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4lCqc2WhSeeeW49RDs7lXfeysj9sKI8rk4yjva3i1fWr) ![Wyatt's Saloon Guest House 2](https://images.trvl-media.com/lodging/105000000/104930000/104923800/104923751/6e1883c5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyatt's Saloon Guest House 2 Fells Point CA $1,070 per person Jan 15 - Jan 18 just found Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104923751&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4nU5IAnuy8WWRcGPq7C2EgyWAcFdQ6R6I8TocOQZd4oX) ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Sonesta Select Newark Christiana Mall](https://images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta Select Newark Christiana Mall 48 Geoffrey Dr, Newark, DE Fully refundableReserve now, pay when you stay CA $142 CA $157 total Nov 17 - Nov 18 includes taxes & fees 7.6/10 Good! (1,150 reviews) Yes and somewhat we did t really interact with the staff. Reviewed on Nov 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=2091&PinnedHotelID=2091&HadPinnedHotel=true®ionId=553248635975872164) ![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 $74 CA $83 total Nov 21 - Nov 22 includes taxes & fees 5/10 (1,001 reviews) I was good for the value. Reviewed on Oct 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=25008&PinnedHotelID=25008&HadPinnedHotel=true®ionId=553248635975872164) ![Red Roof Inn & Suites Newark - University](https://images.trvl-media.com/lodging/1000000/10000/8500/8462/a9782baa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn & Suites Newark - University 1119 S College Avenue, Newark, DE Fully refundableReserve now, pay when you stay CA $97 CA $107 total Nov 4 - Nov 5 includes taxes & fees 5.4/10 (1,030 reviews) The room was clean. The whole place could use some updates, for example the carpeting could have been cleaned or replaced. Curtains had cuts in them and the comforter had a burn hole but we were in a non-smoking room. Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F11%2F2025&endDate=05%2F11%2F2025&selected=8462&PinnedHotelID=8462&HadPinnedHotel=true®ionId=553248635975872164) [See all 626 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®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 ![QR code to download the app](data:image/png;base64,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)