Title: Winsted Vacation Packages 2026 from $469 | Expedia.com [Winsted Travel Guide](https://expedia.com/Winsted.dx3000430645)[Hotels in Winsted](https://expedia.com/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Vacation Rentals in Winsted](https://expedia.com/Winsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[Flights to Winsted](https://expedia.com/Cheap-Flights-To-Winsted.d3000430645.Travel-Guide-Flights)[Car Rentals in Winsted](https://expedia.com/Car-Rentals-In-Winsted.d3000430645.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000430645/bb9cdd61-3489-4aed-b910-e06295b1d904.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winsted Vacations from $469 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Winsted Vacation The easiest way to experience this vibrant city is with a customized Winsted vacation package. Stay in the neighborhood of New Hartford, which is great for nature, history and skiing or choose someplace else — our package deals are all about you. If your trip to Winsted includes a little sightseeing, drop by major attractions such as [Highland Lake](https://www.expedia.com/Highland-Lake-Winsted.d553248635976195024.Vacation-Attraction), [Jerram Winery](https://www.expedia.com/Jerram-Winery-New-Hartford.d553248621532666033.Vacation-Attraction) and [Laurel Lanes](https://www.expedia.com/Laurel-Lanes-Winsted.d553248621532666032.Vacation-Attraction). Whoever you're going away with and whatever you plan to spend, your ultimate Winsted vacation is just clicks away with Expedia. ## The Latest Winsted vacation packages Price found within the past 48 hours. Click for updated prices. ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Milford / New Haven $469 per person Mar 15 - Mar 20 found 13 hours ago Roundtrip flight included Dallas (DFW) to New Haven (HVN) 8.6/10 Excellent! (1,184 reviews) Room was spotless the staff was amazing. Room fully stocked with amenities. Had a great stay! The only down side was there were no microwaves in the rooms. Reviewed on Feb 3, 2026 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven $579 per person Mar 15 - Mar 20 found 13 hours ago Roundtrip flight included Dallas (DFW) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Great location to explore Yale. Quiet, comfortable & smartly appointed. Reviewed on Jan 25, 2026 ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cambria Hotel New Haven University Area West River $471 per person Mar 15 - Mar 20 found 13 hours ago Roundtrip flight included Dallas (DFW) to New Haven (HVN) 8.8/10 Excellent! (966 reviews) Room matched pictures. Front desk people were excey Reviewed on Jan 21, 2026 ![Luxury Apartments by Hyatus at Pierpont](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/1add7dcb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Apartments by Hyatus at Pierpont The Hill $679 per person Mar 15 - Mar 20 found 13 hours ago Roundtrip flight included Dallas (DFW) to New Haven (HVN) 9.4/10 Exceptional! (21 reviews) Very quiet, clean and peaceful accommodation. Enjoyed our stay here. Very spacious apartment with everything you need for a comfortable stay. Felt right at home - away from home. Highly recommend. Reviewed on Jan 7, 2026 ![Cheshire Welcome Inn](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/c0034c2e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheshire Welcome Inn $482 per person Mar 15 - Mar 20 found 13 hours ago Roundtrip flight included Dallas (DFW) to New Haven (HVN) 8.4/10 Very Good! (755 reviews) Clean, comfortable and convenient Reviewed on Jan 30, 2026 Don't see what you're looking for? See all available trips from Columbus to Winsted [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CEF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Winsted #### Winchester Historical Society You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area. [](https://expedia.com/Winchester-Historical-Society-Winsted.d553248621532666031.Vacation-Attraction) ## Winsted Hotel Deals ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Hartford Hotel at Bradley Airport 1 Bradley International Airport Windsor Locks CT Fully refundableReserve now, pay when you stay $229 nightly $263 total Feb 14 - Feb 15 Total with taxes and fees 9/10 Wonderful! (1,007 reviews) Friendly casual staff. Plenty good room. Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F14%2F2026&endDate=2%2F15%2F2026&selected=4632&PinnedHotelID=4632&HadPinnedHotel=true®ionId=3000430645) ![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Farmington Inn & Suites 827 Farmington Ave Farmington CT Fully refundableReserve now, pay when you stay $121 nightly $139 total Feb 14 - Feb 15 Total with taxes and fees 8.8/10 Excellent! (999 reviews) From desk staff Reviewed on Feb 2, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F14%2F2026&endDate=2%2F15%2F2026&selected=10185&PinnedHotelID=10185&HadPinnedHotel=true®ionId=3000430645) ![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 $80 nightly $92 total Feb 15 - Feb 16 Total with taxes and fees 7.8/10 Good! (1,006 reviews) Clean although parking lot not cleaned well always enjoy staying at this facility convenient to everything in the area staff is friendly and accommodating Reviewed on Jan 23, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=151013&PinnedHotelID=151013&HadPinnedHotel=true®ionId=3000430645) [See all 824 properties in Winsted](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=3000430645) 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. ## Find the Best Winsted Vacation Packages ## Winsted Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Bradley Intl. Airport (BDL) | | Population | 7,700 | | Top Sights | [Connecticut Valley Winery](https://www.expedia.com/Connecticut-Valley-Winery-New-Hartford.d553248621532665871.Vacation-Attraction), [Winchester Historical Society](https://www.expedia.com/Winchester-Historical-Society-Winsted.d553248621532666031.Vacation-Attraction) and [Jerram Winery](https://www.expedia.com/Jerram-Winery-New-Hartford.d553248621532666033.Vacation-Attraction) | ## More vacations you might like ![](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.com/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 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![](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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Winsted vacation package cost? ### What are the cheapest months to go to Winsted? ### How many days is enough for Winsted? ### Is it worth booking a vacation package to Winsted? ### How to find the best Winsted package deals? ### Is it cheaper to book a Winsted vacation as a package? ### When to book a vacation package to Winsted? ### Does Expedia offer Book Now, Pay Later Winsted vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Laurel Lanes ](https://www.expedia.com/Laurel-Lanes-Hotels.0-l553248621532666032-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Historical Society ](https://www.expedia.com/Winchester-Historical-Society-Hotels.0-l553248621532666031-0.Travel-Guide-Filter-Hotels) - [Winchester Hotels ](https://www.expedia.com/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels) - [West Hill Lake Hotels ](https://www.expedia.com/West-Hill-Lake-Hotels.d553248635975871940.Travel-Guide-Hotels) - [4 Star Hotels in Riverton 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