Title: 4 Stars Hotels in Chester, Massachusetts from CA $146 - Find Cheap Chester Hotels With 4 Stars | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx6005399)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d6005399.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides) ![This abandoned arch looms sixty-five feet over a beautiful oasis fed by small cascades. It's amazing sight to discover in autumn!](https://images.trvl-media.com/place/6005399/0c1b1cf1-f718-45ae-a4ad-16ba5e76c8dc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/0c1b1cf1-f718-45ae-a4ad-16ba5e76c8dc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-13&endDate=2026-01-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-14&endDate=2026-01-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 4-star hotels ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.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/2000000/1460000/1457800/1457797/8d37b75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (354 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $130 CA $146 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/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) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.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) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (290 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $184 CA $216 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly](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) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (134 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.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) ![Dining](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/07d85fda.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.ca/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.ca/Lenox-Hotels-Seven-Hills-Inn.h15691251.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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.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.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $530 CA $641 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.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) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $542 CA $606 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/2ae49251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/32a90503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/32cb12aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/fbe29a4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) Stockbridge 9.8/10 Exceptional (113 reviews) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna T. [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.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) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby CA $304 CA $339 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.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) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/b5bad44f.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) ### The Inn at Stockbridge [](https://www.expedia.ca/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 CA $331 CA $389 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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) ![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/755fb8cb.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](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.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) Great Barrington 9.2/10 Wonderful (90 reviews) "Beautiful Inn and outstanding chef" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $423 CA $511 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.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) ![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) ![Premium bedding, down comforters, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/7ddf77a7.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.ca/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.ca/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.ca/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.ca/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 riverfront in Chester! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-01-27&endDate=2026-01-28&adults=2®ionId=6005399) ![Frozen Sanderson Brook Falls in Chester ](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=300&h=400&p=1&q=high) Photo by Elizabeth Massa Peroulakis ## Top Chester Hotel Reviews ## Find out more about Chester If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Chester? > - Search for the lowest price from CA $146 ### 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 - More ways to book - [2 Star Hotels in East Village Historic District ](https://www.expedia.ca/2Star-East-Village-Historic-District-Amherst-Hotels.s20-n553248621557920008-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in South End ](https://www.expedia.ca/2Star-South-End-Springfield-Hotels.s20-n898868902485037056-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Foxboro ](https://www.expedia.ca/3Star-Foxboro-Hotels.s30-0-d8136.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Franklin ](https://www.expedia.ca/3Star-Franklin-Hotels.s30-0-d601800.Travel-Guide-Filter-Hotels) - 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