Title: Chesterfield Vacation Packages 2026 from $422 | Expedia.com [Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.com/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.com/Cheap-Flights-To-Chesterfield.d89029.Travel-Guide-Flights)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d89029.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) # Chesterfield Vacations from $422 ## 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 Chesterfield Vacation Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like [Chesterfield Gorge](https://www.expedia.com/Chesterfield-Gorge-Chesterfield.d553248621532666609.Vacation-Attraction), [Swift River](https://www.expedia.com/Swift-River-Massachusetts.d681613380051832832.Vacation-Attraction) and [Petticoat Hill](https://www.expedia.com/Petticoat-Hill-Williamsburg.d553248621532666673.Vacation-Attraction). Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style. ## The Latest Chesterfield vacation packages Price found within the past 48 hours. Click for updated prices. ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/d2b7feac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester $422 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 8.4/10 Very Good! (188 reviews) Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available. Reviewed on Nov 10, 2025 ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### D. Hotel Suites & Spa Save 100% on your flight $480 per person Apr 21 - Apr 28 found 22 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.4/10 Exceptional! (2,242 reviews) There were many good things about the stay however; our room was super close to the interstate and the traffic and trucks starting rolling by at 5:30 am. I searched for earplugs and it was not conducive to easy sleep. I would not stay again unless the room was far away from the highway. Be forewarned. The people were super nice and the room was fine. Not great sleep was not! Reviewed on Feb 27, 2026 ![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonnade Hotel Back Bay Back Bay $556 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.2/10 Wonderful! (2,268 reviews) We stay at the Colonnade fairly regularly because of its convenient location and easy parking. This time we were stuck there because of a blizzard, so we spent more time actually hanging around the hotel. The lobby is really comfortable and cozy with a gas fire and a front wall of glass. The room was also very comfortable, including beds, pillows, bathrobes. We ate breakfast twice at the hotel restaurant and the staff were warm and friendly. Reviewed on Feb 25, 2026 ![Hotel UMass](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/4e423f91_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel UMass Save 100% on your flight $712 per person Apr 21 - Apr 28 found 22 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 8.8/10 Excellent! (1,002 reviews) Convenience of the location Reviewed on Feb 24, 2026 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End Save 100% on your flight $1,000 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Chesterfield [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-27/2026-04-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CEF&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_89029) ### Discover the most popular places to visit in Chesterfield #### Chesterfield Gorge Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area. [](https://expedia.com/Chesterfield-Gorge-Chesterfield.d553248621532666609.Vacation-Attraction) ## Chesterfield Hotel Deals ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### D. Hotel Suites & Spa 1 Country Club Rd Holyoke MA Fully refundableReserve now, pay when you stay $115 nightly $128 total Mar 8 - Mar 9 Total with taxes and fees 9.2/10 Wonderful! (2,205 reviews) There were many good things about the stay however; our room was super close to the interstate and the traffic and trucks starting rolling by at 5:30 am. I searched for earplugs and it was not conducive to easy sleep. I would not stay again unless the room was far away from the highway. Be forewarned. ... Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=89029) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay $121 nightly $136 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (864 reviews) Overcharged and lied to said security deposit was released back but never was Reviewed on Feb 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=89029) ![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites 400 Russell St Hadley MA Fully refundableReserve now, pay when you stay $109 nightly $122 total Mar 22 - Mar 23 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) Clean. Updated. Quiet. Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=558078&PinnedHotelID=558078&HadPinnedHotel=true®ionId=89029) [See all 514 properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F28%2F2026&endDate=3%2F1%2F2026®ionId=89029) 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 Chesterfield Vacation Packages ## Chesterfield Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 1,200 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Historic Northampton](https://www.expedia.com/Historic-Northampton-Northampton.d553248621532666662.Vacation-Attraction), [Academy of Music Theater](https://www.expedia.com/Academy-Of-Music-Theater-Northampton.d6070271.Vacation-Attraction) and [Calvin Theatre and Performing Arts Center](https://www.expedia.com/Calvin-Theatre-And-Performing-Arts-Center-Northampton.d553248621532666663.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) 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![](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 Chesterfield vacation package cost? ### What are the cheapest months to go to Chesterfield? ### How many days is enough for Chesterfield? ### How to find the best Chesterfield package deals? ### Is it cheaper to book a Chesterfield vacation as a package? ### When to book a vacation package to Chesterfield? ### Does Expedia offer Book Now, Pay Later Chesterfield vacation packages? ## Explore a world of travel with Expedia - Lodging 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