Title: Cheshire Vacation Packages 2026 from $304 | 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)[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 $304 ## 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. ![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 $304 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Orlando (MCO) to New Haven (HVN) 8.8/10 Excellent! (966 reviews) Room matched pictures. Front desk people were excey Reviewed on Jan 21, 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 Save 100% on your flight $348 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Orlando (MCO) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Cute, old-timey styled room with a nice bathroom. Nice staff. Close to everything. Loved the electric tea pot and the convenient plugs in the nightstand. However, the room was on the small side, and you could feel the cold air coming through the window even with the shades down. I would not recommend staying here on a Friday or Saturday night, though. I was on the second floor and I was kept up until well past 2:00 am due to a group of loud students hanging out on the sidewalk for several hours…in 20 degree weather! Reviewed on Feb 8, 2026 ### Landing Modern 2bd, Gym West New Haven $717 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Norfolk (ORF) to New Haven (HVN) No reviews ![Luxury Furnished Apartments by Hyatus Downtown at Yale](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/a842220e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Furnished Apartments by Hyatus Downtown at Yale The Hill $700 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Norfolk (ORF) to New Haven (HVN) 9.6/10 Exceptional! (60 reviews) Cleaning good although some of the furniture and carpets show a lot of wear for a new building. Definitely would stay there again. Reviewed on Jan 12, 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/2026-03-10/2026-03-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BDL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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) #### Cheshire Hollow Farm Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area. [](https://expedia.com/Cheshire-Hollow-Farm-Cheshire.d553248621561886472.Vacation-Attraction) #### Cheshire Golf Course Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theater scene in this romantic area. [](https://expedia.com/Cheshire-Golf-Course-Cheshire.d553248621563220877.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 $111 nightly $128 total Feb 22 - Feb 23 Total with taxes and fees 9/10 Wonderful! (2,020 reviews) Clean, well designed rooms. Reviewed on Feb 2, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%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 $93 nightly $107 total Feb 11 - Feb 12 Total with taxes and fees 7.4/10 Good! (1,167 reviews) Glad Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=6777&PinnedHotelID=6777&HadPinnedHotel=true®ionId=183057) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel New Haven University Area 20 Dwight Street New Haven CT Fully refundable $107 nightly $123 total Mar 8 - Mar 9 Total with taxes and fees 8.6/10 Excellent! (1,009 reviews) Lovely Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=183057) [See all 1,238 properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F11%2F2026&endDate=2%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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[4 Star Hotels in Meriden ](https://www.expedia.com/4Star-Meriden-Hotels.s40-0-d8818.Travel-Guide-Filter-Hotels) - [Flights to Prospect ](https://www.expedia.com/Cheap-Flights-To-Prospect.d6004525.Travel-Guide-Flights) - [Flights to Plantsville ](https://www.expedia.com/Cheap-Flights-To-Plantsville.d6084748.Travel-Guide-Flights) - [Flights to Meriden ](https://www.expedia.com/Cheap-Flights-To-Meriden.d8818.Travel-Guide-Flights) - [Flights to Wallingford ](https://www.expedia.com/Cheap-Flights-To-Wallingford.d7533.Travel-Guide-Flights) - [Flights from Meriden ](https://www.expedia.com/lp/flights/8818/flights-from-meriden) - [Flights from Orlando to Meriden ](https://www.expedia.com/lp/flights/178294/8818/orlando-to-meriden) - [Maplecroft Plaza Shopping Center ](https://www.expedia.com/Maplecroft-Plaza-Shopping-Center-Cheshire.d553248621557931242.Vacation-Attraction) - [Visit Cheshire Historic District ](https://www.expedia.com/Cheshire-Historic-District.dx6346724) - [Cheshire Golf Course ](https://www.expedia.com/Cheshire-Golf-Course-Cheshire.d553248621563220877.Vacation-Attraction) - 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