Title: The Best 4 Star Hotels in Chester, MA from $114 | 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) ![](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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester 4 Star Hotels Tonight [Mar 29 - Mar 30](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-29&endDate=2026-03-30&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 30 - Mar 31](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-30&endDate=2026-03-31&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 4-star hotels ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED | Individually furnished, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (359 reviews) "Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TIFFANY $102 nightly $114 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/870ad54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (295 reviews) "Friendly staff, great location, beautiful views, cozy room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $151 nightly $169 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.com/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah $335 nightly $374 total Apr 11 - Apr 12 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Room #10 Queen's Cottage | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.com/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (137 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $329 nightly $367 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/c5b973e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/88348850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge [](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) Lee 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $238 nightly $266 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/9d4b10ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/ee47037f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/3c58b600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/ceae03ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seven Hills Inn [](https://www.expedia.com/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) Lenox 7.8/10 Good (467 reviews) "Great location, nice breakfast and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.com/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Thayer House, Room 201, 1 King bed, Jetted tub | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/f1d5c4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/6afab6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Thayer House, Room 201, 1 King bed, Jetted tub | Living area | 32-inch TV with cable channels](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/05269ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Inn On The Green [](https://www.expedia.com/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) Great Barrington 9.2/10 Wonderful (91 reviews) "Beautiful Inn and outstanding chef" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine $336 nightly $368 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Every point of contact I had at 33 Main was friendly, efficient, and accommodating. It’s evident Donna and her team run the inn with love. It’s clean and gorgeously furnished on the inside. You’ll recognize it from the outside, because it’s the most charmingly decorated on the block. I stayed in the Cliffwood room, which was the perfect size for me as a solo traveler (in other words, although smaller than the other rooms, it did not feel too small). The room and private bathroom were clean and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanthana $445 nightly $498 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/f5dca788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.com/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (44 reviews) "Comfortable bed. Quiet location. Excellent breakfast. Friendly host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen $252 nightly $281 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/0eb6e44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/f210c5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/ac720fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/00d33bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garden Gables Inn [](https://www.expedia.com/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) Lenox 9.2/10 Wonderful (57 reviews) "Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john [](https://www.expedia.com/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) ![](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%2F4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) ## Learn more about Chester Experience the hiking, camping, and monuments in Chester! [See all hotels in Chester](https://www.expedia.com/Hotel-Search?startDate=2026-04-12&endDate=2026-04-13&adults=2®ionId=6005399) ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=473&h=473&p=1&q=high) Photo by Chris Addams ## Top Chester Hotel Reviews ## Find out more about Chester ## Chester Four Star Hotel Information When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service. Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop. Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Chester? > - Search for the lowest price from $114 ### What's the difference between 5-star and 4-star hotels in Chester? ### Does Chester have any 4-star all-inclusive resorts? ## 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) - [4 Star Hotels in Middlefield ](https://www.expedia.com/4Star-Middlefield-Hotels.s40-0-d132966.Travel-Guide-Filter-Hotels) - [Hotels near Sherwood Forest ](https://www.expedia.com/Sherwood-Forest-Becket-Hotels.0-n553248635976472129-0.Travel-Guide-Filter-Hotels) - [Hotels near Littleville Lake ](https://www.expedia.com/Littleville-Lake-Hotels.0-l553248621532666607-0.Travel-Guide-Filter-Hotels) - 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