Title: Winchester Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?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 When a city stay is calling, answer it with a vacation package to Winchester. With all your travel needs organized before you leave, all you need to do here is focus on having a ball. If a sightseeing tour is on the to-do list during your trip to Winchester, look around leading attractions like [Thomas Aquinas College](https://www.expedia.ca/Thomas-Aquinas-College-Northfield.d553248635974560181.Vacation-Attraction), [Pisgah State Park](https://www.expedia.ca/Pisgah-State-Park-New-Hampshire.d637212810858491904.Vacation-Attraction) and [Birch Point](https://www.expedia.ca/Birch-Point-United-States-of-America.d553248635975749057.Vacation-Attraction). Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester vacation plans into motion! ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Colonial Hotel 625 Betty Spring Road Gardner MA Fully refundableReserve now, pay when you stay 8.8/10 Excellent! (1,001 reviews) Friendly staff, clean room, gym and poll area. Reviewed on Feb 4, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true®ionId=3000447144) [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true®ionId=3000447144) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Brattleboro I-91 1186 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $168 CA $185 total Mar 5 - Mar 6 includes taxes & fees 8.4/10 Very Good! (760 reviews) Nice location… clean room! Breakfast was not appetizing… Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=8784377&PinnedHotelID=8784377&HadPinnedHotel=true®ionId=3000447144) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Brattleboro 1378 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $156 CA $171 total Mar 1 - Mar 2 includes taxes & fees 8.2/10 Very Good! (940 reviews) Recently renovated room Reviewed on Jan 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=1158047&PinnedHotelID=1158047&HadPinnedHotel=true®ionId=3000447144) [See all 462 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®ionId=3000447144) 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) ## 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