Title: Winchester Vacation Packages & Trips 2026 from CA $531 | 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! ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Colonial Motel And Spa CA $531 per person Jun 19 - Jun 22 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Springfield (VSF) 6.8/10 (1,006 reviews) It was good to have pool option after a ski day Reviewed on Mar 10, 2026 ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Latchis Hotel CA $643 per person Jun 19 - Jun 22 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Springfield (VSF) 8.6/10 Excellent! (853 reviews) If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful! This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back! Reviewed on Mar 30, 2026 ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Covered Bridge Inn CA $624 per person Jun 19 - Jun 22 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Springfield (VSF) 7.6/10 Good! (1,007 reviews) Decent Internet. Room stayed warm. Reviewed on Mar 9, 2026 ![Black Mountain Inn](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/05d203e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Black Mountain Inn CA $723 per person Jun 19 - Jun 22 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Springfield (VSF) 7.4/10 Good! (486 reviews) Pet friendly for $15 plus tax. The place noisy with heat turned on in the room Reviewed on Mar 20, 2026 ![Econo Lodge Brattleboro South](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/de359926_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Econo Lodge Brattleboro South CA $566 per person Jun 19 - Jun 22 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Springfield (VSF) 5.4/10 (621 reviews) Near food and shopping, ac and heater work good. Reviewed on Jan 22, 2026 ## 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/ad889baf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Colonial Hotel 625 Betty Spring Road Gardner MA Fully refundableReserve now, pay when you stay CA $200 CA $224 total Apr 5 - Apr 6 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Comfortable bed, everything was neat and tidy. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true®ionId=3000447144) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Colonial Motel And Spa 889 Putney Rd Brattleboro VT Fully refundableReserve now, pay when you stay CA $132 CA $145 total Apr 5 - Apr 6 includes taxes & fees 6.8/10 (1,000 reviews) Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone ... Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=1070729&PinnedHotelID=1070729&HadPinnedHotel=true®ionId=3000447144) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Brattleboro 1378 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $181 CA $200 total Apr 17 - Apr 18 includes taxes & fees 8.2/10 Very Good! (955 reviews) Nice Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F04%2F2026&endDate=18%2F04%2F2026&selected=1158047&PinnedHotelID=1158047&HadPinnedHotel=true®ionId=3000447144) [See all 470 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F04%2F2026&endDate=05%2F04%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