Title: Visit Chesterfield: 2026 Travel Guide for Chesterfield, Massachusetts | Expedia.com [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)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d89029.Destination-Travel-Guides) # Chesterfield, MA ## Travel Guide ## Visit Chesterfield Things to do ![](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=DX_SPRING_PROMO_89029) - Chesterfield Hotel Deals - Vacation Rentals in Chesterfield ![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 $121 nightly $135 total Mar 11 - Mar 12 Total with taxes and fees Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (2,225 reviews) This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar. Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F11%2F2026&endDate=3%2F12%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 refundable $115 nightly $128 total Apr 9 - Apr 10 Total with taxes and fees Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ... 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%2F9%2F2026&endDate=4%2F10%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 $109 nightly $122 total Mar 22 - Mar 23 Total with taxes and fees Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 9.2/10 Wonderful! (1,012 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.DestinationExperience&startDate=3%2F11%2F2026&endDate=3%2F12%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. ![Peace and quiet on the lake](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2959f9e4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peace and quiet on the lake Becket MA Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ... 9.6/10 Exceptional! (234 reviews) Host was great! Quick communication. Place is a gem for peace and tranquility! The home is beautiful with great view. Reviewed on Feb 18, 2026 [](https://expedia.com/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Elm Suite with a Private Bathroom in front of Smith College Quadrangle](https://images.trvl-media.com/lodging/77000000/76670000/76663400/76663304/w527h682x257y1-cbfd4b54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elm Suite with a Private Bathroom in front of Smith College Quadrangle Northampton MA Stay at this apartment in Northampton. Enjoy in-room jetted tubs, an in-room coffeemaker, and air conditioning. Popular attractions Smith College Botanic Garden ... 9.8/10 Exceptional! (26 reviews) Our stay here was amazing! The host was great about checking in and was super responsive. The room is quaint and cozy. The bathtub was perfect for a romantic weekend getaway. We both have back problems and the bed was comfortable and we both woke up pain free. We will definitely be back! Thanks for ... Reviewed on Mar 1, 2026 [](https://expedia.com/Northampton-Hotels-Elm-Suite-With-A-Private-Bathroom-In-Front-Of-Smith-College-Quadrangle.h76663304.Hotel-Information) ![Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/51d20e21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating Becket MA Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ... 9.6/10 Exceptional! (236 reviews) A wonderful weekend getaway. Cabin is very clean and the wood stove is wonderful. Reviewed on Mar 8, 2026 [](https://expedia.com/Becket-Hotels-Quiet-Comfortable-Cabin-5-Min-Walk-To-Swimming-And-Boating.h19210630.Hotel-Information) [See all properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=89029&sort=VACATION_RENTAL) 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. ## Check Chesterfield hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=2026-03-10&endDate=2026-03-11)[Mar 10 - Mar 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=2026-03-10&endDate=2026-03-11) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=2026-03-11&endDate=2026-03-12)[Mar 11 - Mar 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=2026-03-11&endDate=2026-03-12) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89029&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) ### Popular places to visit #### 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 Public Library Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops. [](https://expedia.com/Chesterfield-Public-Library-Chesterfield.d909393830101508096.Vacation-Attraction) #### Krug Sugarbush You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops. [](https://expedia.com/Krug-Sugarbush-Chesterfield.d909392809247760384.Vacation-Attraction) ## Cities near Chesterfield ![Beautiful waterfalls nestled away in the countryside. ](https://images.trvl-media.com/place/132966/5e95a670-722b-45e6-8d54-96fabaf4303c.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Huntington ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Western Massachusetts Hotels ](https://www.expedia.com/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels) - [Resorts & Hotels with Spas in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Spa-Hotel.0-0-d6234063-tSpaHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Luxury-Hotel.0-0-d6234063-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Romantic-Hotel.0-0-d6234063-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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