Title: Chesterfield, MA Cottage Rentals | 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 In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterfield cottages ![Living area](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/bd43511e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/243a2493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/6712b9ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/6ba55a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2-bedroom cottage on Robert Frost Trail [](https://www.expedia.com/Amherst-Hotels-Beautiful-2-Bedroom-Cottage-On-Robert-Frost-Trail.h124273112.Hotel-Information) Amherst $237 nightly $265 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Amherst-Hotels-Beautiful-2-Bedroom-Cottage-On-Robert-Frost-Trail.h124273112.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=2026-02-20&endDate=2026-02-20®ionId=89029&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CABIN) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VILLA) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America®ionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CHALET) ![](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-Cottages.d89029-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Cottages.d89029-aaCottages.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![Inn on Boltwood](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f10073da_y.jpg) ### Inn on Boltwood 10/10 Excellent "Great stay. Convenient location on the edge of campus in town. Comfortable room. Friendly staff. Free parking. Excellent dinner at 30Boltwood. Highly recommend!" [](https://expedia.com/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information) ![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg) ### Fairfield Inn & Suites Springfield Northampton/Amherst 10/10 Excellent "Gorgeous room amazing stay" [](https://expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Room was clean and nicely equipped with kitchen. Will return if the future. " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg) ### Quality Inn & Suites Northampton - Amherst 10/10 Excellent "Great room, very clean and welcoming, helpful staff. Breakfast was pretty good too!" [](https://expedia.com/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information) ![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg) ### Hotel Northampton 10/10 Excellent "The staff were amazing and the room was perfect. " [](https://expedia.com/Springfield-Hotels-Hotel-Northampton.h17876.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 "Great hotel to stay in. Staff is super friendly and pays attention to a details. Rooms are kept fresh and clean. I will return in future" [](https://expedia.com/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back " [](https://expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "All good. Strange stay as there was a large storm approaching." [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Comfortable room, great breakfast with cozy fireplace. Friendly and efficient staff. Easy parking. Walkable area amidst Smith College and fifteen minute walk to downtown Northampton attractions and restaurants. " [](https://expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Cottages information | Number of reviews | | | ----------------- | -------- | | Accommodation | Cottages | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Why book your cottage in Chesterfield with Expedia? ### How can I find cheap cottages in Chesterfield? ### What is there to do in Chesterfield near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Cabins.d6234063-aaCabins.Travel-Guide-Accommodation) - [B&B in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Bed-And-Breakfast.d6234063-aaBedAndBreakfast.Travel-Guide-Accommodation) - [RV Parks in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-RV-Parks.d6234063-aaRVParks.Travel-Guide-Accommodation) - 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