Title: The Best Hotels Closest to Chesterwood in South Lee - 2026 Updated Prices | Expedia.co.uk [Holiday Rentals in South Lee](https://expedia.co.uk/South-Lee-Holiday-Rentals.d183343.Travel-Guide-HolidayRentals)[Chesterwood Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chesterwood.d6091841.Car-Hire-Guide)[Chesterwood Holidays](https://expedia.co.uk/Chesterwood-South-Lee.d6091841.Attraction) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/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 prices for these dates Tonight [10 Feb - 11 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6091841&startDate=2026-02-10&endDate=2026-02-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [11 Feb - 12 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6091841&startDate=2026-02-11&endDate=2026-02-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6091841&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6091841&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Our top choices for Chesterwood hotels ![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) ![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) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) 0.4 mi from Chesterwood 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 £274 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/fa13e671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) 2.1 mi from Chesterwood 8.8/10 Excellent (1,003 reviews) "As always, our stay at The Red Lion Inn was memorable. Everything was top notch." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary £152 includes taxes & fees 10 Mar - 11 Mar [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) 3.6 mi from Chesterwood 9.6/10 Exceptional (445 reviews) "The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carin £90 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/25fee020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/2ff1c815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/835e48b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/6d6ce66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Granville House [](https://www.expedia.co.uk/Housatonic-Hotels-Granville-House.h50873824.Hotel-Information) 4 mi from Chesterwood 10/10 Exceptional (94 reviews) "Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer £142 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Housatonic-Hotels-Granville-House.h50873824.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) ![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) ![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) ### The Inn at Stockbridge [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) 3.2 mi from Chesterwood 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £205 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms | Iron/ironing board, free cots/infant beds, WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) 4.1 mi from Chesterwood 9.0/10 Wonderful (833 reviews) "Great overnights stay, wish I was here longer " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas £106 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1c5bd04f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/c93f6ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires [](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) 5.3 mi from Chesterwood 9.4/10 Exceptional (767 reviews) "Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dinh £123 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) 5 mi from Chesterwood 8.8/10 Excellent (731 reviews) "Great property, very accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shanice £87 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![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) ![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.co.uk/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) 4.7 mi from Chesterwood 10/10 Exceptional (135 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.co.uk/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.co.uk/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) 3.2 mi from Chesterwood 8.6/10 Excellent (553 reviews) "Great friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo £90 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) 5.4 mi from Chesterwood 9.0/10 Wonderful (820 reviews) "The room was clean, and the staff was friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damien [](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/e112ee1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/08a849e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn [](https://www.expedia.co.uk/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) 5.4 mi from Chesterwood 9.6/10 Exceptional (374 reviews) "Amazing customer service! Location was very good to explore the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophia [](https://www.expedia.co.uk/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cots/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/0f74ae3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee - Lenox South [](https://www.expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) 5.7 mi from Chesterwood 8.4/10 Very good (1,001 reviews) "Safe, clean rooms, decent breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil £69 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/51ca9ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.co.uk/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) 6.3 mi from Chesterwood 9.6/10 Exceptional (37 reviews) "The room was clean and comfortable wi will back next year:) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadya £102 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![In-room safe, desk, free cots/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, free cots/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.co.uk/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) 3.8 mi from Chesterwood 7.6/10 Good (567 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad £61 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/390a52f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/bb325877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Valley Motel West Stockbridge [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) 2.9 mi from Chesterwood 6.8/10 (1,001 reviews) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne £47 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/8801cfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/4c6ff871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/dc04db42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires [](https://www.expedia.co.uk/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) 6.7 mi from Chesterwood 9.0/10 Wonderful (1,002 reviews) "The Inn was very nice and the staff was super friendly and attentive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £112 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/5e996a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/w4000h2033x0y0-e62570a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/36a39838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Lenox Berkshires [](https://www.expedia.co.uk/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) 7.5 mi from Chesterwood 9.2/10 Wonderful (599 reviews) "Our stay was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gianna £107 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) 8.1 mi from Chesterwood 9.0/10 Wonderful (855 reviews) "So charming, clean, thoughtful touches and a really special place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana £72 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![In-room dining](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/ca66a901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/fd5f12a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f0e5252a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cots/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/017819f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Lee - Great Barrington [](https://www.expedia.co.uk/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) 4.6 mi from Chesterwood 6.4/10 (658 reviews) "The room was clean and the service adequate" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £52 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.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.co.uk/Hotel-Search?startDate=2026-02-24&endDate=2026-02-25®ionId=6091841&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Compare popular hotels close to Chesterwood | Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | | | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | ----------------- | ------------------------- | ------------------ | ---- | --- | ------------ | ------------- | | | ![Suite, Private Bathroom (RedBird Suite) \| View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 4.5 star property | 9.2Wonderful110 reviews | View | | | | | | | ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)The Red Lion Inn | 3.5 star property | 8.8Excellent1,003 reviews | View | | | | | | | ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Shaker Mill Inn | 2.5 star property | 9.6Exceptional445 reviews | View | | | | | | | ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/25fee020.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Granville House | 3.0 star property | 10.0Exceptional94 reviews | View | | | | | | | ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)The Inn at Stockbridge | 4.0 star property | 9.8Exceptional99 reviews | View | | | | | | ## Top Chesterwood Hotel Reviews ![The Little Lion](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef_y.jpg) ### The Little Lion 10/10 Excellent "Great friendly staff" [](https://expedia.co.uk/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. " [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions](https://images.trvl-media.com/lodging/103000000/102010000/102001500/102001430/b9eabd0d_y.jpg) ### Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions 10/10 Excellent "This is a really lovely, well-kept house. The layout is wonderful, offering plenty of space for everyone to spread out, while also having ample room for spending time all together. There is so much attention to detail (like delicious treats for us on the dining table!), well-stocked kitchen and bathrooms, and plenty of comfortable seating. The host was so nice and extremely responsive each time I reached out. We loved this house and would definitely stay again!" [](https://expedia.co.uk/Stockbridge-Hotels-Charming-Cape-Cod-Home-In-Prime-Berkshire-Location-5-Minutes-To-Tanglewood.h102001430.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 "Great overnights stay, wish I was here longer " [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay](https://images.trvl-media.com/lodging/106000000/105020000/105019600/105019545/a7b5f2d0_y.jpg) ### Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay 10/10 Excellent "Great property and very responsive host" [](https://expedia.co.uk/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information) ![Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://images.trvl-media.com/lodging/93000000/92110000/92100700/92100621/369ddb1e_y.jpg) ### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10 10/10 Excellent "We had a great time at the Taggart River House! Views and light were unbelievable and it was so nice to be there with extended family and have everyone have their own lovely spaces with bathrooms. A quick walk into town made the days even richer. Would 100% stay again! Also well stocked for kids with a high chair, crib, etc. only missing one stair gate which would have made it perfect, but we put furniture in front of those stairs and that was a great solution too. " [](https://expedia.co.uk/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.Hotel-Information) ![A Grand property in Historic Stockbridge](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7_y.jpg) ### A Grand property in Historic Stockbridge 10/10 Excellent "Great stay!" [](https://expedia.co.uk/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) ![Stockbridge Home, Come Experience The Berkshires!](https://images.trvl-media.com/lodging/88000000/87640000/87633700/87633659/b5ee0956_y.jpg) ### Stockbridge Home, Come Experience The Berkshires! 10/10 Excellent "Fully equipped. Pet friendly" [](https://expedia.co.uk/Stockbridge-Hotels-Stockbridge-Home.h87633659.Hotel-Information) ![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 10/10 Excellent "It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!" [](https://expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ## Hotels near other Chesterwood attractions ### Norman Rockwell Museum 4.7/5 (252 reviews) You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6091839) ### Berkshire Botanical Garden 4.0/5 (1 review) Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665247) ### Mission House You can spend time studying the exhibits at Mission House in Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621560941222) ### Naumkeag Museum 3.5/5 (2 reviews) You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6091843) ### National Shrine of the Divine Mercy 4.5/5 (54 reviews) Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665250) ### Schantz Galleries You can spend an afternoon studying the exhibits at Schantz Galleries during your travels in Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665248) ### Art et Industrie You can spend an afternoon exploring the galleries in Art et Industrie during your trip to Great Barrington. Amble around this quaint area's gardens or seek out the hiking trails. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665245) ### Berkshire Theatre Festival You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665249) ## Frequently asked questions ### What's the area like around Chesterwood? ### Where is the best place to stay close to Chesterwood? ### How many hotels will I find near Chesterwood? ### If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund? ### What can I see and do near Chesterwood?