Title: Chesterfield Vacation Packages 2026 from $574 | 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 $574 ## 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. ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End Save 100% on your flight $574 per person May 14 - May 16 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 8.6/10 Excellent! (1,384 reviews) Good location to T.D. Garden. Reviewed on Mar 7, 2026 ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/f9b493e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester Save 100% on your flight $883 per person Apr 13 - Apr 17 found 1 day ago Roundtrip flight included Dallas (DFW) 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 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston Save 100% on your flight $1,031 per person May 22 - May 25 found 1 day ago Roundtrip flight included Chicago (ORD) to Boston (BOS) 9.6/10 Exceptional! (251 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/6c2b250e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge Save 100% on your flight $1,177 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.4/10 Exceptional! (1,003 reviews) Room and staff were great Reviewed on Feb 26, 2026 ![Life House, Nantucket](https://images.trvl-media.com/lodging/49000000/48530000/48529300/48529240/a9cbc478_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Life House, Nantucket Nantucket Town Save 100% on your flight $890 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Miami (MIA) to Boston (BOS) 8/10 Very Good! (65 reviews) The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again. Reviewed on Sep 26, 2025 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/2026-04-09/2026-04-16/?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/1000000/850000/849400/849303/8974a65a_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 $121 nightly $135 total Mar 10 - Mar 11 Total with taxes and fees 9.2/10 Wonderful! (2,224 reviews) We have stayed several times. I was rather disappointed this past weekend. The elevator was dirty and had a horrible, shirilling noise when opening and closing. Our room had black hair strands all over the blanket and under the blanket. The sink did not empty properly and had flakes of something ... Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=89029) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay $115 nightly $128 total Apr 8 - Apr 9 Total with taxes and fees 9/10 Wonderful! (870 reviews) This was great. I did not really need the kitchen for my stay but for future planning this wil be great! Plenty of room in the living area. Bed was comfortable. Just beautiful Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=89029) ![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Hadley - Amherst 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! (1,011 reviews) Beautiful view from rooftop pool Reviewed on Mar 8, 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=3%2F10%2F2026&endDate=3%2F11%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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