Title: Chester, MA Villas Rentals | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6005399)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6005399.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d6005399.Destination-Travel-Guides) ![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.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 [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester villas ![Property grounds](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/79e104d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/ed6f8836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/7a56f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Whately [](https://www.expedia.com/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information) 10/10 Exceptional (8 reviews) "Thanks for a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea M. $677 nightly $756 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.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=2026-03-16&endDate=2026-03-17®ionId=6005399&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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=AA_SPRING_PROMO_6005399) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CABIN) Villas [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VILLA) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=COTTAGE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&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%2FChester-Villas.d6005399-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Villas.d6005399-aaVillas.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Simple and clean hotel" [](https://expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Residence Inn Springfield Chicopee](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/6d969748_y.jpg) ### Residence Inn Springfield Chicopee 10/10 Excellent "Clean room, friendly staff. " [](https://expedia.com/Springfield-Hotels-Residence-Inn-Springfield-Chicopee.h6250331.Hotel-Information) ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "What a lovely hotel - kind staff, hearty breakfast, beautiful place - would stay again. Only qualm is that the heater is quite loud." [](https://expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Overall pleasant stay; great facilities, staff, and location" [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "Staff was super helpful and hospitable! Shout out to Jim! We were here during a blizzard and they actually cleaned the snow off of our car! Room was lovely and clean. Great breakfast. " [](https://expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Clean room, breakfast was good👍" [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Courtyard by Marriott West Springfield](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "Clean, safe, great spot, friendly staff. Always a joy to stay there. " [](https://expedia.com/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very spacious and comfortable. Great for families." [](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Affordable price, clean bedroom and close to everything. " [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Chester ## Chester Villas information | Number of reviews | 8 | | ----------------- | -------- | | Accommodation | 2 Villas | | Lowest Price | $756 | | Highest Price | $756 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Becket Land Trust Historic Quarry ](https://www.expedia.com/Becket-Land-Trust-Historic-Quarry-Hotels.0-l553248621532666600-0.Travel-Guide-Filter-Hotels) - [B&B in Middlefield ](https://www.expedia.com/Middlefield-Bed-And-Breakfast.d132966-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Resorts in Middlefield ](https://www.expedia.com/Middlefield-Resorts.d132966-aaResorts.Travel-Guide-Accommodation) - [Condo Resorts in Middlefield ](https://www.expedia.com/Middlefield-Condominium-Resort.d132966-aaCondominiumResort.Travel-Guide-Accommodation) - [Hotels near Sherwood Forest ](https://www.expedia.com/Sherwood-Forest-Becket-Hotels.0-n553248635976472129-0.Travel-Guide-Filter-Hotels) - 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