Title: Winchester Vacation Packages & Trips 2026 from CA $525 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.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 The best way to experience this unique city is with a tailor-made Winchester vacation package. Base yourself in the neighborhood of New Hartford, which is good for nature, history and skiing or choose someplace else — our package deals are all about you. Make your trip to Winchester even more enjoyable by going sightseeing. [Highland Lake](https://www.expedia.ca/Highland-Lake-Winsted.d553248635976195024.Vacation-Attraction), [Laurel Lanes](https://www.expedia.ca/Laurel-Lanes-Winsted.d553248621532666032.Vacation-Attraction) and [Winchester Historical Society](https://www.expedia.ca/Winchester-Historical-Society-Winsted.d553248621532666031.Vacation-Attraction) are some of the leading attractions you'll want to explore. Whatever your travel plans or budget, organizing your ultimate tailored Winchester vacation is easy with Expedia. ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/4c692d71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 Milford, CT CA $525 per person Apr 2 - Apr 6 found 8 hours ago Roundtrip flight included Montreal (YMQ) to New Haven (HVN) 6.2/10 (1,000 reviews) Nice service and clean room Reviewed on Feb 16, 2026 ![Mayflower Motel Milford](https://images.trvl-media.com/lodging/2000000/1730000/1721900/1721807/d9e240b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mayflower Motel Milford CA $543 per person Apr 2 - Apr 6 found 8 hours ago Roundtrip flight included Montreal (YMQ) to New Haven (HVN) 6/10 (549 reviews) We are staying here for a few nights to be close to my family. We drove by Mayflower Motel so many times. We always stayed at a hotel that we were familiar with, big named places Reviewed on Nov 30, 2025 ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 New Haven - Branford, CT CA $553 per person Apr 2 - Apr 6 found 8 hours ago Roundtrip flight included Montreal (YMQ) to New Haven (HVN) 7/10 Good! (1,001 reviews) The room was very clean. Would stay again Reviewed on Feb 21, 2026 ![Super 8 by Wyndham Milford/New Haven](https://images.trvl-media.com/lodging/1000000/870000/866400/866321/f1ba5603_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Milford/New Haven CA $589 per person Apr 2 - Apr 6 found 8 hours ago Roundtrip flight included Montreal (YMQ) to New Haven (HVN) 5.6/10 (891 reviews) The room was nice for the price like the fact no tub it's a stand up shower Reviewed on Jan 2, 2026 ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor CA $558 per person Apr 2 - Apr 6 found 8 hours ago Roundtrip flight included Montreal (YMQ) to New Haven (HVN) 8/10 Very Good! (1,002 reviews) nice people helpful and friendly. bathroom needs bit of work..... Reviewed on Feb 19, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635975869849) ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Extended Stay America Suites Hartford Farmington 1 Batterson Park Rd Farmington CT Fully refundableReserve now, pay when you stay CA $111 CA $127 total Feb 23 - Feb 24 includes taxes & fees 8/10 Very Good! (1,004 reviews) The room was spartan but very clean. The bed is comfortable. The hotel is near the highway but far enough to be very quiet. Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=151013&PinnedHotelID=151013&HadPinnedHotel=true®ionId=553248635975869849) ![Delamar West Hartford](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delamar West Hartford 1 Memorial Road West Hartford CT Fully refundableReserve now, pay when you stay CA $405 CA $486 total Mar 1 - Mar 2 includes taxes & fees 9.8/10 Exceptional! (1,003 reviews) Great as always Reviewed on Feb 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=18166744&PinnedHotelID=18166744&HadPinnedHotel=true®ionId=553248635975869849) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Hartford/Farmington 301 Colt Hwy Farmington CT Fully refundableReserve now, pay when you stay CA $167 CA $192 total Feb 28 - Mar 1 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) they didn’t have a room for me, send me to another hotel that didn’t have the same amenities. i didn’t have to pay for the room, they gave me a full credit, however, they didn’t inform me until i got to the hotel, i should have gotten an email or a call, and i was very unhappy that their was no hot ... Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=2970540&PinnedHotelID=2970540&HadPinnedHotel=true®ionId=553248635975869849) [See all 689 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026®ionId=553248635975869849) 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