Title: The 10 Best Hotels Near Chesterwood, South Lee from CA $88 | Expedia.ca [South Lee Travel Guide](https://expedia.ca/South-Lee.dx183343)[Vacation Rentals in South Lee](https://expedia.ca/South-Lee-Vacation-Rentals.d183343.Travel-Guide-VacationRentals)[Chesterwood Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterwood.d6091841.Car-Rental-Guide)[Chesterwood Vacations](https://expedia.ca/Chesterwood-South-Lee.d6091841.Vacation-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__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 prices for these dates Tonight [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-03-24&endDate=2026-03-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-03-25&endDate=2026-03-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## 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) ![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) ![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.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) 0.6 km 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 CA $425 CA $514 total includes taxes & fees Apr 18 - Apr 19 [](https://www.expedia.ca/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) ![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) ![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) 3.3 km from Chesterwood 8.8/10 Excellent (1,000 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 [](https://www.expedia.ca/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)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) 5.8 km from Chesterwood 9.6/10 Exceptional (446 reviews) "Had everything we needed. Very thoughtful touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $143 CA $157 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) 8 km from Chesterwood 8.8/10 Excellent (749 reviews) "Simple and clean hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vitor CA $147 CA $164 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.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) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.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.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) 6.6 km from Chesterwood 9.0/10 Wonderful (856 reviews) "Room was awesome and very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryanashley CA $154 CA $199 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.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) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) 5.1 km from Chesterwood 8.6/10 Excellent (555 reviews) "Clean … check in , good location for us .. we’ll be back in Maynn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $148 CA $166 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) 8.6 km from Chesterwood 9.2/10 Wonderful (1,002 reviews) "Room was spotless, staff was very kind!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilia CA $131 CA $146 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) 8.7 km from Chesterwood 9.0/10 Wonderful (834 reviews) "Nice place and very reasonable for great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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) ![Interior detail](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/6d6ce66a.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) ![Garden](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/2ff1c815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Granville House [](https://www.expedia.ca/Housatonic-Hotels-Granville-House.h50873824.Hotel-Information) 6.4 km from Chesterwood 10/10 Exceptional (97 reviews) "Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $239 CA $267 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Housatonic-Hotels-Granville-House.h50873824.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.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) ![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) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) 8.6 km from Chesterwood 9.4/10 Exceptional (774 reviews) "Staff was lovely, everything was easy, clean and comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helena CA $209 CA $233 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.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.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) 5.2 km 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 CA $328 CA $384 total includes taxes & fees Apr 18 - Apr 19 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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) ![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) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/c24971a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee - Lenox South [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) 9.1 km from Chesterwood 8.4/10 Very good (1,000 reviews) "Cleanliness, staff courtesy, breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $115 CA $129 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Room #10 Queen's Cottage | Living room](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.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) ![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 #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) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) 7.5 km from Chesterwood 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 [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![In-room safe, desk, free cribs/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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) 6.2 km from Chesterwood 7.6/10 Good (574 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad CA $103 CA $115 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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) ![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) ![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.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.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) 8.7 km from Chesterwood 9.6/10 Exceptional (376 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.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Desk, laptop workspace, blackout drapes, 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.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) ### Pleasant Valley Motel West Stockbridge [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) 4.7 km from Chesterwood 6.8/10 (1,000 reviews) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $80 CA $88 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) 12.5 km from Chesterwood 9.8/10 Exceptional (23 reviews) "Friendly staff, beautiful interiors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Izabela CA $191 CA $213 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](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) ![Classic Double Room, 2 Queen Beds, Courtyard View](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.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.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) 10.1 km from Chesterwood 9.4/10 Exceptional (40 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 CA $176 CA $197 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.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) ![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/77000000/76300000/76297700/76297618/967b0257.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.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) 13 km from Chesterwood 9.0/10 Wonderful (880 reviews) "Beautiful little quaint hotel. I will definitely be returning" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin CA $96 CA $107 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/047ef967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/28728ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/25c9c72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitlock [](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) 9.8 km from Chesterwood 8.6/10 Excellent (292 reviews) "Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elaine CA $150 CA $167 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.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.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®ionId=6091841&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Compare popular hotels close to Chesterwood | Property | Star rating | 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 | 8.8Excellent1,000 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 | 9.6Exceptional446 reviews | View | | | | | | | ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Holiday Inn Express Hotel & Suites Great Barrington by IHG | 2.5 star property | 8.8Excellent749 reviews | View | | | | | | | ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 3.5 star property | 9.0Wonderful856 reviews | View | | | | | | ## Top Chesterwood Hotel Reviews ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great place to enjoy with the whole family!!!" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Little Lion](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540_y.jpg) ### The Little Lion 8/10 Good "Great location for everything" [](https://expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Walk into town, soak up sun on enclosed porch & steps away from nature trails!](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7_y.jpg) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! 10/10 Excellent "A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!" [](https://expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Stockbridge pied-à-terre](https://images.trvl-media.com/lodging/101000000/100940000/100935100/100935011/b342bccc_y.jpg) ### Stockbridge pied-à-terre 10/10 Excellent "Linda was terrific and communicated promptly place was perfect for my Writers Retreat giving me space and plenty of light. I recommend it, A lovely property." [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Pied-A-Terre.h100935011.Hotel-Information) ![Family Ski Getaway in the Berkshires](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1_y.jpg) ### Family Ski Getaway in the Berkshires 10/10 Excellent "Loved our time here. It was a very cozy set up for a snowy week away, with a pellet stove, an ample amount of puzzles stocked in the house, and the surprise perk of Studley, a 12 year old cuddle machine of a cat who lives here and provided great company. The host was very responsive to all of my messages, and had the driveway promptly plowed in the inclimate weather " [](https://expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg) ### The Red Lion Inn 10/10 Excellent "great customer service" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://images.trvl-media.com/lodging/93000000/92110000/92100700/92100621/7d7eb623_y.jpg) ### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10 10/10 Excellent "The house was great! We stayed with kids, and there were even games for them to play, which was an added bonus. " [](https://expedia.ca/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.Hotel-Information) ![Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay](https://images.trvl-media.com/lodging/106000000/105020000/105019600/105019545/73e267de_y.jpg) ### Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay 10/10 Excellent "Great property and very responsive host" [](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information) ![A Grand property in Historic Stockbridge](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/0152068c_y.jpg) ### A Grand property in Historic Stockbridge 10/10 Excellent "Great stay!" [](https://expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) ## Hotels near other Chesterwood attractions ### Norman Rockwell Museum 4.7/5 (252 reviews) You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665247) ### Mission House You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621560941222) ### Naumkeag Museum 3.5/5 (2 reviews) You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside. [See properties](https://www.expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665250) ### Schantz Galleries You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665248) ### Art et Industrie You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665245) ### Berkshire Theatre Festival You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665249) ## Frequently asked questions ### What are the top-rated hotels near Chesterwood? > [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information) > > > Taggart Treehouse offers a luxurious escape with breathtaking river views, just 3.2 km from Chesterwood. Rated an impressive 10 by travellers, this modern retreat accommodates up to 10 travellers, perfect for larger groups. Guests can enjoy amenities such as a fully equipped kitchen with a dishwasher, oven, and coffee maker, along with a spacious patio and garden area for relaxation. > > > [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information) > > > Located 4.7 km from Chesterwood, the Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8\. This historic hotel combines charm with modern comforts, featuring a well-equipped kitchen, outdoor play areas, and nearby hiking trails. Guests can unwind on the patio or explore local attractions such as wineries and ski resorts, making it a versatile choice for all travellers. > > > [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) > > > The Inn at Stockbridge is a 4-star gem just 6.6 km from Chesterwood, rated 9.8 by travellers. Guests can indulge in complimentary cooked breakfasts and relax by the outdoor pool. With a variety of amenities, including a spa, fitness facilities, and beautifully designed rooms with premium bedding, this inn perfectly blends comfort and elegance, creating a peaceful retreat amidst the stunning Berkshire landscape. ### What hotels are within walking distance to Chesterwood? > [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) > > > The Stockbridge Country Inn is a charming 4.5-star bed and breakfast located just a 12-minute walk from Chesterwood, with an excellent review rating of 9.2\. Guests can enjoy delightful amenities such as complimentary breakfast options, an onsite art gallery, and a terrace for relaxation. Outdoor enthusiasts will appreciate the hiking and biking trails nearby, along with a golf course located just a short distance away. The inn boasts a luxurious historic design, complete with premium bedding and a fireplace, ensuring a comfortable and memorable stay. ### How much is a hotel near Chesterwood? ### What are the most popular family-friendly hotels near Chesterwood? > [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information) > > > Taggart Treehouse: Modern Luxury Meets Nature is only 3.2 km from Chesterwood and enjoys a perfect 10 travellers' rating. This unique hotel offers a cozy kitchen and a lovely patio, perfect for family gatherings. With a travel crib and stair gate for children, it ensures safety and comfort for younger travellers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind. > > > [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information) > > > Vacation in a Berkshire Farmhouse is a fantastic option just 4.7 km from Chesterwood, an impressive travellers' rating of 9.8\. This inviting farmhouse features amenities tailored for families, including a spacious kitchen, outdoor play area for children, and a variety of toys to keep the little ones entertained. With a beautiful garden and patio, parents can relax while kids explore. Guests also enjoy nearby hiking, skiing, and antique shopping. > > > [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) > > > Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 7.6 km from Chesterwood, offers a family-friendly environment with a review rating of 9.0 and a 3.5-star rating. Families will appreciate the onsite playground, arcade game room, and spacious rooms equipped with kitchen facilities and a crib at no extra charge. Guests can also take advantage of the indoor and outdoor pools, hot tub, and nearby skiing activities for a fun-filled family holidays. ### Which hotels near Chesterwood offer the best views? > [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information) > > > Located just 4.7 km from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travellers. Guests can relish breathtaking mountain views from the patio and enjoy outdoor adventures, including hiking and skiing nearby. The hotel features a fully equipped kitchen, a cozy garden, and ample parking, making it a perfect retreat for nature lovers who appreciate rustic charm. > > > [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) > > > Just a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travellers. Guests are treated to scenic mountain views from the terrace and can indulge in complimentary full breakfasts. With amenities like a pool, hiking options on-site, and a charming historic design, this inn provides a cozy and luxurious feel, making it an ideal spot for art and nature enthusiasts alike. > > > [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) > > > This 3.5-star resort is situated 7.6 km from Chesterwood and boasts a review rating of 9.0\. Guests can take advantage of the outdoor and indoor pools, hot tubs, and on-site tennis courts. The resort's balconies and patios offer lovely resort views, perfect for relaxation after a day of exploring. With family-friendly amenities and a variety of activities, it's a delightful choice for those looking to enjoy the Berkshires. ### What are the best affordable hotels near Chesterwood? > [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information) > > > Taggart Treehouse is a spacious retreat just 3.2 km from Chesterwood, rated an impressive 10 by travellers. This hotel features stunning river views and is perfect for families or groups, providing amenities like a fully equipped kitchen with a dishwasher and an oven, plus a cozy patio to enjoy the outdoors. Guests can also benefit from onsite parking and WiFi, ensuring a comfortable stay. > > > [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information) > > > Just 4.7 km from Chesterwood, Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8\. This family-friendly farmhouse features an outdoor play area for children and is surrounded by opportunities for hiking, skiing, and winery tours. Guests can enjoy a kitchen equipped with modern appliances, a charming patio, and WiFi to stay connected during their stay. > > > [Shaker Mill Inn](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) > > > Located 7.9 km from Chesterwood, Shaker Mill Inn is a cozy escape with a review rating of 9.6\. This inn offers a free breakfast and self-parking, making it a convenient choice for travellers. Guests can relax in their rooms featuring a kitchenette and enjoy the beautiful garden or the private hot tub. With contactless check-in and a warm atmosphere, it's a delightful option for a restful stay. ### Are there any hotels with pools close to Chesterwood? > [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) > > > The Inn at Stockbridge, just 6.6 km from Chesterwood, is a sophisticated 4-star retreat with an outstanding review rating of 9.8\. This hotel features a serene outdoor pool surrounded by beautiful gardens, ideal for relaxation. Guests are treated to complimentary breakfast and access to a 24-hour fitness centre, ensuring a comfortable and energizing stay. > > > [The Red Lion Inn](https://expedia.ca/Stockbridge-hotels-The-Red-Lion-Inn.h5780784.Hotel-information) > > > Located only 3.7 km from Chesterwood, The Red Lion Inn boasts a charming 3.5-star experience with a review rating of 8.8\. Guests can unwind in the outdoor pool area, featuring comfortable sun loungers. This historic hotel offers a variety of amenities including a spa, 24-hour room service, and easy access to skiing and snowboarding activities, perfect for those looking to explore the nearby mountains. > > > [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) > > > Situated just 7.6 km from Chesterwood, the Holiday Inn Club Vacations Oak n' Spruce Resort is a family-friendly gem with an impressive review rating of 9.0\. Guests can enjoy both indoor and outdoor pools, complete with sun loungers and a poolside bar for leisurely afternoons. Additional highlights include a hot tub, mini-golf, and on-site tennis facilities, making it an ideal choice for families and outdoor enthusiasts alike. ### What are the best pet-friendly hotels near Chesterwood? > [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information) > > > Just 4.7 km from Chesterwood, Vacation in a Berkshire Farmhouse is an idyllic retreat for pet owners, allowing pets in-room. With an outstanding review rating of 9.8, this farmhouse boasts a historic charm and offers a plethora of amenities that include a kitchen, outdoor play area for children, and nearby hiking opportunities. Guests can unwind on the patio or explore local attractions, making it an excellent choice for families and travellers with pets alike. > > > [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) > > > The Inn at Stockbridge, located 6.6 km from Chesterwood, is a charming 4-star hotel that welcomes dogs only. With a remarkable review rating of 9.8, this inn features an outdoor pool, spa services, and a lovely garden area, perfect for relaxing with pets. Guests can indulge in a complimentary cooked breakfast and enjoy comfortable accommodations with premium bedding and designer toiletries, ensuring a delightful stay for both you and your furry friend. > > > [Econo Lodge Lee - Great Barrington](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) > > > Econo Lodge Lee - Great Barrington is just 8.0 km from Chesterwood and offers a cozy stay for travellers with pets. This budget-friendly hotel allows pets in-room, making it a great choice for those traveling with furry companions. Guests can enjoy amenities like daily housekeeping, free continental breakfast, and access to a mini-golf course on-site. Rated by travellers at 6.4, it's a convenient option for families looking to explore the beautiful Berkshire region. ### Can I book a fully refundable hotel close to Chesterwood? ### Can I find Expedia discounts for hotels near Chesterwood? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [3 Star Hotels in Stockbridge ](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [Guest Houses in Alford ](https://www.expedia.ca/Alford-Guest-Houses.d3000421226-aaGuestHouses.Travel-Guide-Accommodation) - [Alford Hotels ](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Lodges in Alford ](https://www.expedia.ca/Alford-Lodges.d3000421226-aaLodges.Travel-Guide-Accommodation) - [Hotels near Berkshire Botanical Garden ](https://www.expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) - [Berkshire County Hotels ](https://www.expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations) - 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