Title: 20 Best B&B in Chesterfield, MA - Bed and Breakfast from $194 | 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)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d89029.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterfield bed & breakfast ![Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/ab4ff31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/857f2ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/b58e5c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Quadruple Room, 2 Queen Beds | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/8797adfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Walnut Inn [](https://www.expedia.com/Amherst-Hotels-Black-Walnut-Inn.h106114099.Hotel-Information) North Amherst 9.8/10 Exceptional (112 reviews) "Beautiful Inn. Love the old brick front and antiques. The staff was amazing, breakfast was delicious and the rooms were spotless. The molasses cookies at check in were a bonus. Loved our stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosemarie $178 nightly $199 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Amherst-Hotels-Black-Walnut-Inn.h106114099.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/177e0ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/4c325a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Non Smoking, River View | Living area | 40-inch LCD TV with cable channels, TV, Hulu](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/006ae3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639314/4a306dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Mill Inn [](https://www.expedia.com/Springfield-Hotels-Old-Mill-Inn.h1639314.Hotel-Information) Hatfield 9.4/10 Exceptional (505 reviews) "Quality Inn feeling with wonderful continental breakfast and very clean- well appointed quiet room! Would definitely stay there again on our next visit to Smith College " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barry $179 nightly $200 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Old-Mill-Inn.h1639314.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/542dbb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Shared Dormitory | Free WiFi](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/f69b88ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/3033684f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UU Rowe Camp and Conference Center [](https://www.expedia.com/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information) Rowe 10/10 Exceptional (1 review) "Yes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart $225 nightly $238 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/fc57caa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/522cc3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daniel Stebbins Room #2 | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/79ed918f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daniel Stebbins Room #2 | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/7a3b2f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daniel Stebbins House [](https://www.expedia.com/South-Hadley-Hotels-Daniel-Stebbins-Bed-And-Breakfast.h34814366.Hotel-Information) South Hadley 10/10 Exceptional (51 reviews) "Quaint B&B in the heart of South Hadley. Within walking distance of town and Mount Holyoke College. (Stairs to second floor are a bit steep for anyone with accessibility issues.) Great overall local place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason $270 nightly $302 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/South-Hadley-Hotels-Daniel-Stebbins-Bed-And-Breakfast.h34814366.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/d0afa322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![28-inch TV with digital channels, Netflix, pay movies](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/0db93a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trail in Adams - Berkshires’ Art Hotel [](https://www.expedia.com/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) Adams 9.0/10 Wonderful (145 reviews) "Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) selmin $174 nightly $194 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams) | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53 reviews) "Nice place for a weekend away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory $231 nightly $244 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-14&endDate=2026-04-15®ionId=89029&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Bed-And-Breakfast.d89029-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Bed-And-Breakfast.d89029-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "We love this hotel so much, we have stayed here twice. The breakfast has a nice variety and is good quality. We enjoyed relaxing in the large hot tub at night. The staff is friendly and helpful. " [](https://expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Easy to book, clean room, close to entertainment and restaurants, has a pool and hot tub. " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg) ### Blue – A Modern Hotel, an Ascend Collection Hotel 10/10 Excellent "Great parking" [](https://expedia.com/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ![Candlewood Suites West Springfield by IHG](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/537cea4c_y.jpg) ### Candlewood Suites West Springfield by IHG 8/10 Good "." [](https://expedia.com/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.Hotel-Information) ![Courtyard by Marriott Hadley Amherst](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/978d1151_y.jpg) ### Courtyard by Marriott Hadley Amherst 10/10 Excellent "Not used. Had pre made yougurt. Good" [](https://expedia.com/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information) ![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg) ### Comfort Inn & Suites Hadley - Amherst 10/10 Excellent "Clean room and sufficient place to sleep. The pillows were comfortable and the staff were very polite. We appreciated the GF options for breakfast and the small fitness center. We had a nice dinner at a location recommend by the hotel as well. " [](https://expedia.com/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/58b2bc45_y.jpg) ### Quality Inn West Springfield 6/10 Okay "The breakfast was not that best. The eggs were watery. The matress" [](https://expedia.com/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Good hotel! Would stay here again!" [](https://expedia.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Motel 6 Chicopee, MA - Springfield](https://images.trvl-media.com/lodging/1000000/1000000/996200/996151/e70677eb_y.jpg) ### Motel 6 Chicopee, MA - Springfield 4/10 Poor "Tbh rough times " [](https://expedia.com/Springfield-Hotels-Motel-6-Chicopee.h996151.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield B&B information | Number of reviews | 867 | | ----------------- | ----- | | Accommodation | 8 B&B | | Lowest Price | $194 | | Highest Price | $302 | ## Frequently asked questions ### Searching for B&Bs in Chesterfield? ### How do you know if a B&B is the best choice for your stay? ### What are the top B&Bs in Chesterfield? ### What's the best time of year to stay at a B&B in Chesterfield? ### What is there to do in Chesterfield? ### How can I get to and around Chesterfield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - 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