Title: Chesterfield Vacation Packages 2026 from $493 | 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 $493 ## 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. ![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/54848539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonnade Hotel Back Bay Back Bay Save 100% on your flight $493 per person Jun 5 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.2/10 Wonderful! (2,282 reviews) Very good location, desk staff pleasant would definitely recommend Reviewed on Mar 22, 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 $914 per person May 7 - May 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.8/10 Exceptional! (1,001 reviews) Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub. Reviewed on Mar 23, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston Save 100% on your flight $891 per person May 29 - Jun 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch. Bed was nice and very quiet location. Reviewed on Mar 22, 2026 ![The Cove at Yarmouth by Westgate Resorts](https://images.trvl-media.com/lodging/1000000/10000/4400/4331/ac25d19b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cove at Yarmouth by Westgate Resorts $536 per person May 28 - May 31 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Boston (BOS) 9.2/10 Wonderful! (254 reviews) Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time. Reviewed on Jan 31, 2026 ![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 $1,102 per person Jun 18 - Jun 21 found 9 hours ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 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/2026-04-24/2026-05-01/?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 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 refundable $134 nightly $149 total Mar 26 - Mar 27 Total with taxes and fees 9.4/10 Exceptional! (2,220 reviews) The staff were very friendly, making the entire stay pleasant from check-in to check-out. The hotel was clean and well-maintained, and the surroundings were quiet, which made it easy to relax. The room was also quite spacious, providing plenty of comfort during the stay. It’s a great choice for anyone ... Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&selected=849303&PinnedHotelID=849303&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 refundable $120 nightly $134 total Apr 1 - Apr 2 Total with taxes and fees 9.2/10 Wonderful! (1,006 reviews) N/A Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=558078&PinnedHotelID=558078&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 $108 nightly $120 total Apr 23 - Apr 24 Total with taxes and fees 9/10 Wonderful! (885 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F23%2F2026&endDate=4%2F24%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=89029) [See all 514 properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F25%2F2026&endDate=3%2F26%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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