Title: Chesterfield Vacation Packages 2026 from $614 | 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 $614 ## Book a Hotel + Flight or Car together to unlock savings ## 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 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 $614 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Boston (BOS) 9.2/10 Wonderful! (257 reviews) From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months - The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing. Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable. Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future. Reviewed on Mar 29, 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 $1,461 per person Jun 17 - Jun 22 found 4 hours ago Roundtrip flight included Los Angeles (LAX) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![Life House, Nantucket](https://images.trvl-media.com/lodging/49000000/48530000/48529300/48529240/48c398ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Life House, Nantucket Nantucket Town Save 100% on your flight $1,204 per person May 20 - May 26 found 1 day ago Roundtrip non-stop flight included Denver (DEN) 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 ![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 $1,211 per person May 16 - May 18 found 1 day ago Roundtrip non-stop flight included Dallas (DAL) to Boston (BOS) 9.8/10 Exceptional! (1,003 reviews) From the moment we arrived we knew we made the right decision. The property is beautiful and the staff are professional and friendly. We were very pleased with our room and the great view of Boston Harbor. Two minor issues were the water spot on the bathroom sinks were too short for the size of the sink, making it hard to use without making a mess (wide designs such things and knows). The other minor item was the quality of the toilet tissue, for a hotel of this caliber, the need to spend a little more there. I must say that these were minor issues considering how amazing this property is. We went to the Dark Bar twice and loved it, had breakfast in the hotel restaurant and couldn’t have been more pleased and also had room service dinner one night and were very impressed. I would highly recommend this property! Reviewed on Apr 6, 2026 ![By the Sea Guests Bed & Breakfast & Suites](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/97cdd647_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### By the Sea Guests Bed & Breakfast & Suites Save 100% on your flight $842 per person May 20 - May 26 found 1 day ago Roundtrip non-stop flight included Denver (DEN) to Boston (BOS) 9.2/10 Wonderful! (185 reviews) Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year! Reviewed on Sep 20, 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/2026-05-07/2026-05-14/?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 $150 nightly $168 total Apr 8 - Apr 9 Total with taxes and fees 9.4/10 Exceptional! (2,231 reviews) I personally loved everything about the hotel. You walked in and it was very clean and the staff was super friendly and very informative. The room was very clean and spacious and the Wi-Fi was fast and there was no buffering. The breakfast was really nice and yummy. There were free, orange juice ... Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%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 $108 nightly $120 total May 7 - May 8 Total with taxes and fees 9/10 Wonderful! (895 reviews) Love that place. Does need a little sprucing up. Staff great and accomodating Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=5%2F7%2F2026&endDate=5%2F8%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 refundable $127 nightly $141 total Apr 20 - Apr 21 Total with taxes and fees 9.2/10 Wonderful! (1,009 reviews) Excellent breakfast for a quick unexpected benefit Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F20%2F2026&endDate=4%2F21%2F2026&selected=558078&PinnedHotelID=558078&HadPinnedHotel=true®ionId=89029) [See all 512 properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F8%2F2026&endDate=4%2F9%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://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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