Title: Cheshire Vacation Packages 2026 from $385 | Expedia.com [Cheshire Travel Guide](https://expedia.com/Cheshire.dx183057)[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.com/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.com/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Things to do in Cheshire](https://expedia.com/Things-To-Do-In-Cheshire.d183057.Travel-Guide-Activities)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cheshire Vacations from $385 ## 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 Cheshire Vacation There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire vacation packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like [Toyota Oakdale Theatre](https://www.expedia.com/Toyota-Presents-Oakdale-Theatre-Wallingford.d6089829.Vacation-Attraction), [Choate Rosemary Hall](https://www.expedia.com/Choate-Rosemary-Hall-Wallingford.d553248635939586716.Vacation-Attraction) and [Mount Southington Ski Area](https://www.expedia.com/Mount-Southington-Ski-Area-Plantsville.d6089845.Vacation-Attraction). Expedia will help you escape your daily routine. Tailor your vacation to Cheshire to suit your style of travel, whatever that may look like. ## The Latest Cheshire vacation packages Price found within the past 48 hours. Click for updated prices. ![Clarion Inn North Haven - New Haven North](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/26c48632_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Clarion Inn North Haven - New Haven North $385 per person May 16 - May 19 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to New Haven (HVN) 7.6/10 Good! (1,001 reviews) Amazing staff and rooms Reviewed on Feb 15, 2026 ![Beechmont - Perfect for Family Retreat!](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beechmont - Perfect for Family Retreat! North End Save 100% on your flight $1,083 per person Apr 10 - Apr 12 found 1 day ago Roundtrip flight included Raleigh (RDU) to New Haven (HVN) No reviews ![Hyatus Luxury Residences City Crossing](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/2e7a06d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatus Luxury Residences City Crossing The Hill Save 100% on your flight $1,854 per person May 16 - May 19 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to New Haven (HVN) 9.2/10 Wonderful! (29 reviews) Communication and ease Reviewed on Mar 8, 2026 ![Luxury Furnished Apartments by Hyatus Downtown at Yale](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/695af8be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Furnished Apartments by Hyatus Downtown at Yale The Hill Save 100% on your flight $2,037 per person May 16 - May 19 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to New Haven (HVN) 9.6/10 Exceptional! (64 reviews) Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best. Reviewed on Feb 27, 2026 ![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Executive Hotel Of New Haven - West Haven Save 100% on your flight $499 per person May 16 - May 19 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to New Haven (HVN) 8/10 Very Good! (1,564 reviews) Great overnight stay. Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Cheshire [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-10/2026-04-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BDL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](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.com/deals?rfrr=PKG_SPRING_PROMO_183057) ### Discover the most popular places to visit in Cheshire ![Roaring Brook Falls in the forest](https://images.trvl-media.com/place/553248621561886458/81c4c0f1-3c4f-41a4-8ad6-f6ed5e14b7b6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Roaring Brook Park Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene. [](https://expedia.com/Roaring-Brook-Park-Cheshire.d553248621561886458.Vacation-Attraction) #### Barker Character, Comic and Cartoon Museum You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area. [](https://expedia.com/Barker-Character-Cheshire.d6269046.Vacation-Attraction) #### Maplecroft Plaza Shopping Center You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene. [](https://expedia.com/Maplecroft-Plaza-Shopping-Center-Cheshire.d553248621557931242.Vacation-Attraction) ## Cheshire Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundableReserve now, pay when you stay $85 nightly $98 total Mar 30 - Mar 31 Total with taxes and fees 9/10 Wonderful! (2,035 reviews) the fan in the bathroom was not working and noisey Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=183057) ![The Capitol Hotel](https://images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Capitol Hotel 440 Asylum St Hartford CT Fully refundableReserve now, pay when you stay $101 nightly $117 total Mar 29 - Mar 30 Total with taxes and fees 7.6/10 Good! (1,194 reviews) I travel frequently and am comfortable staying in modest hotels as long as they are clean and safe. Unfortunately, The Capitol Hotel in Hartford raised serious safety concerns and appears to be significantly misrepresented online. The property does not resemble the photos on Expedia. The exterior ... Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=6777&PinnedHotelID=6777&HadPinnedHotel=true®ionId=183057) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane Milford CT Fully refundableReserve now, pay when you stay $101 nightly $116 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (1,272 reviews) The King size bed was fine, We requested the mattress on the convertible couch to be changed, and they accommodated us. Staff was very service oriented. Included breakfast was very good. The room was clean, quite spacious, and comfortable. As in most places, noise can be an issue with paper thin ... Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=183057) [See all 1,282 properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F11%2F2026&endDate=3%2F12%2F2026®ionId=183057) 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 Cheshire Vacation Packages ## Cheshire Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Tweed - New Haven Regional Airport (HVN) | | Population | 29,400 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Lake Compounce](https://www.expedia.com/Lake-Compounce-Southington.d6089781.Vacation-Attraction), [Toyota Presents Oakdale Theatre](https://www.expedia.com/Toyota-Presents-Oakdale-Theatre-Wallingford.d6089829.Vacation-Attraction) and [Powder Ridge Mountain Park and Resort](https://www.expedia.com/Powder-Ridge-Mountain-Park-And-Resort-Connecticut.d553248621560918651.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 [](https://expedia.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.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 Cheshire vacation package cost? ### What are the cheapest months to go to Cheshire? ### How many days is enough for Cheshire? ### Is it worth booking a vacation package to Cheshire? ### How to find the best Cheshire package deals? ### Is it cheaper to book a Cheshire vacation as a package? ### When to book a vacation package to Cheshire? ### How to plan a trip to Cheshire? > 1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Cheshire. > 2. Plan your budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Cheshire. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Cheshire: Research every part of your trip to Cheshire with this comprehensive planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings. > 4. Decide how many days away: Start by compiling a list of the sights and activities you'd like to get to in Cheshire. Then, estimate how long you'll need at each, as well as any travel time. > 5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Cheshire vacation package that brings all your bookings together. > 6. Add on excursions and experiences: Read our dedicated travel guide to find some awesome [things to do in Cheshire](https://www.expedia.com/Things-To-Do-In-Cheshire.d183057.Travel-Guide-Activities). Book tickets or make reservations before you go to save time and skip the hassle of searching for activities once you arrive. ### Does Expedia offer Book Now, Pay Later Cheshire vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Maplecroft Plaza Shopping Center ](https://www.expedia.com/Maplecroft-Plaza-Shopping-Center-Hotels.0-l553248621557931242-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District ](https://www.expedia.com/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - [3 Star Hotels in Cheshire Historic District ](https://www.expedia.com/3Star-Cheshire-Historic-District-Hotels.s30-0-d6346724.Travel-Guide-Filter-Hotels) - [Vacation Homes in Cheshire Historic District ](https://www.expedia.com/Cheshire-Historic-District-Private-Vacation-Homes.d6346724-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels near Drazen Orchards ](https://www.expedia.com/Drazen-Orchards-Hotels.0-l553248621561886358-0.Travel-Guide-Filter-Hotels) - 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