Title: Best Hotels Near Chesterwood, South Lee from CA $94 | 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) # Find hotels near Chesterwood, South Lee from CA $94 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Hotels Close to Chesterwood ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.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) ![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) ![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 0.6 km from Chesterwood 9.2/10 Wonderful (105) "Great breakfast, friendly helpful staff, pretty yard, good location " CA $428 CA $518 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn 3.3 km from Chesterwood 8.8/10 Excellent (1007) "great place have stayed several times, and hope to return." CA $239 CA $330 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Room, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 6.6 km from Chesterwood 9.0/10 Wonderful (735) "The lodging was convenient to all the area attractions." CA $173 CA $213 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.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/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel 8.7 km from Chesterwood 9.0/10 Wonderful (756) "Good value for the price" CA $107 CA $119 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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 (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) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn 5.8 km from Chesterwood 9.6/10 Exceptional (427) "Very casual and easy check in and out; lovely and substantial breakfast" CA $248 CA $273 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/1e5f2e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ebf28595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/36b54e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion 5.1 km from Chesterwood 8.6/10 Excellent (533) "Comfy, quiet, and clean " CA $136 CA $152 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge 5.2 km from Chesterwood 9.8/10 Exceptional (98) "Well-run and elegant property. " CA $550 CA $645 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Standard Room](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/4c557ede.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 8 km from Chesterwood 8.8/10 Excellent (664) "Very Good; Clean, Quiet Motel, Area has many dining options." CA $172 CA $192 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.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/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn 9.2 km from Chesterwood 8.4/10 Very good (1006) "Very convenient off I 90 - nice breakfast area - friendly staff" CA $129 CA $144 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/bb325877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Pleasant Valley Motel West Stockbridge 4.7 km from Chesterwood 6.8/10 (1007) "good average place to stay." CA $85 CA $94 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.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/16000000/15790000/15783300/15783244/21cb26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn 8.7 km from Chesterwood 9.6/10 Exceptional (282) "The staff are absolutely wonderful. The inn is beautiful and so well cared for. And bonus the lake views are gorgeous!" CA $215 CA $253 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.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) ![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) ### Travelodge by Wyndham Great Barrington Berkshires 6.2 km from Chesterwood 7.6/10 Good (549) "Excellent location, friendly service, clean, comfortable room." CA $104 CA $116 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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 #10 Queen's Cottage | Private kitchen](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/bbf9b83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/2d151170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B 7.5 km from Chesterwood 10/10 Exceptional (129) "The inn has an excellent location and amenities." CA $497 CA $555 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/a9be6743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn 10.3 km from Chesterwood 8.4/10 Very good (1001) "Great location and close enough to walk to shops and restaurants. " CA $129 CA $144 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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) ![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) ![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.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) ### Chambery Inn 8.7 km from Chesterwood 9.6/10 Exceptional (369) "ease of late check in. Super comfortable room." CA $313 CA $349 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Premium Apartment | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/c0c5a00b.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) ### East Rock Inn 10.1 km from Chesterwood 9.4/10 Exceptional (32) "Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. " CA $197 CA $221 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/0fb6095c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/6727f40e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/31526127.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) ### Econo Lodge Lee - Great Barrington 7.4 km from Chesterwood 6.4/10 (633) "This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area." CA $89 CA $100 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/62000000/61550000/61548200/61548158/4e239755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/62000000/61550000/61548200/61548158/a170be3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/62000000/61550000/61548200/61548158/8e218a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, Balcony, Mountain View (Orchard)](https://images.trvl-media.com/lodging/62000000/61550000/61548200/61548158/aed29151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apple Tree Inn 8.2 km from Chesterwood 8.6/10 Excellent (306) "Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. " CA $229 CA $256 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Lenox-Hotels-Apple-Tree-Inn.h61548158.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.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) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold 13 km from Chesterwood 9.0/10 Wonderful (730) "Rooms are a clean and upgraded motel. Nice lobby and rooms. " CA $177 CA $198 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Tanglewood Suite)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn 9.1 km from Chesterwood 9.4/10 Exceptional (160) "Inn was gorgeous and staff exceptional!" CA $283 CA $316 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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=2025-10-09&endDate=2025-10-10®ionId=6091841&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterwood Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Walk into town, soak up sun on enclosed porch & steps away from nature trails!](//images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238_y.jpg) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! 10/10 Excellent "The property is absolutely beautiful and extremely well appointed. It is even more beautiful than the photos. It is in a quiet and central location. Julie, the host is attentive, professional and very helpful. I will be coning back for sure. " [](https://expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Stockbridge pied-à-terre](//images.trvl-media.com/lodging/101000000/100940000/100935100/100935011/99becd58_y.jpg) ### Stockbridge pied-à-terre 10/10 Excellent "Very nice and beautifully decorated. Bed comfortable I would recommend 2 things however. Get rid of the rocker in the bedroom and put in a simple chair for those who have difficulty putting on shoes. Second I would suggest that a floor lamp in the living room so that you don’t have to put on the ceiling lights. " [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Pied-A-Terre.h100935011.Hotel-Information) ![Secluded Family Home in Serene Stockbridge Woods](//images.trvl-media.com/lodging/34000000/33670000/33660100/33660074/abf132cf_y.jpg) ### Secluded Family Home in Serene Stockbridge Woods 10/10 Excellent "Lovely easy living home in the Berkshires. Fantastic location. The house is on a nice quiet road close to everything we wanted to do—Tanglewood, Shakespeare and Co, kayaking on the Stockbridge Bowl….. Tom was very responsive to our questions. And this house has a wonderful back porch. We spent most evenings and mornings there" [](https://expedia.ca/West-Stockbridge-Hotels-Tranquil-Getaway-In-The-Stockbridge-Woods-Warm.h33660074.Hotel-Information) ![Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay](//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 "Woodland Zen was supper clean, well maintained and perfectly located. Our property manager, Roberto, was very responsive and helpful and made our stay a true pleasure." [](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information) ![Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions](//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 "Lovely home, great location. The grounds, outdoor dining setup, etc. were all terrific." [](https://expedia.ca/Stockbridge-Hotels-Charming-Cape-Cod-Home-In-Prime-Berkshire-Location-5-Minutes-To-Tanglewood.h102001430.Hotel-Information) ![Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge](//images.trvl-media.com/lodging/118000000/117970000/117968500/117968482/f7665b54_y.jpg) ### Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge 10/10 Excellent "Great place. Exactly as described." [](https://expedia.ca/Stockbridge-Hotels-Brand-NEW-Charming-2-Bedroom-Apartment-With-WiFi.h117968482.Hotel-Information) ![A Grand property in Historic Stockbridge](//images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7_y.jpg) ### A Grand property in Historic Stockbridge 10/10 Excellent "Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand." [](https://expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) ![Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10](//images.trvl-media.com/lodging/93000000/92110000/92100700/92100621/369ddb1e_y.jpg) ### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10 8/10 Good "Very nice house" [](https://expedia.ca/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.Hotel-Information) ### Hotels near Other South Lee Attractions [](https://expedia.ca/Norman-Rockwell-Museum-Hotels.0-l6091839-0.Travel-Guide-Filter-Hotels) ![Norman Rockwell Museum](https://mediaim.expedia.com/destination/2/8f946ea40f181d64f9531da690351b5f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Norman Rockwell Museum 4.5/5(6 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6091839) [](https://expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels) ![Tanglewood Music Center](https://mediaim.expedia.com/destination/2/dc62d836ac629aa2331a99f59e618f75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tanglewood Music Center 5/5(6 reviews) You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=503292) [](https://expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) #### Berkshire Botanical Garden 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665247) [](https://expedia.ca/Mission-House-Hotels.0-l553248621560941222-0.Travel-Guide-Filter-Hotels) #### Mission House You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621560941222) [](https://expedia.ca/Naumkeag-Museum-Hotels.0-l6091843-0.Travel-Guide-Filter-Hotels) #### Naumkeag Museum 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6091843) [](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Hotels.0-l553248621532665250-0.Travel-Guide-Filter-Hotels) #### National Shrine of the Divine Mercy 5/5(1 review) 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665250) ## Frequently asked questions ### What's the area like around Chesterwood? > Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, check out the 10 hotels and other accommodations you'll find within a mile. ### What's the best hotel to stay close 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) is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Other good choices within a few miles include [The Red Lion Inn](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) and [Tanglewood Suites](https://www.expedia.ca/Stockbridge-Hotels-Tanglewood-Suites.h38291154.Hotel-Information). ### How many hotels are there close to Chesterwood? > Expedia has 10 hotels and other accommodations within a mile from Chesterwood. ### If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund? > Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood. ### Where can I learn more about changing or cancelling my trip in the area near Chesterwood? > For more information about picking new dates or cancelling your stay near Chesterwood, head over to [our customer service page](https://www.expedia.com/service/). ### What can I see and do near Chesterwood? > You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount, and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery, and Charles H. Baldwin & Sons while you're out sightseeing 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) - [Farmstay in Glendale](https://www.expedia.ca/Glendale-Agritourism.d901769277689110528-aaAgritourism.Travel-Guide-Accommodation) - [Apartments in Glendale](https://www.expedia.ca/Glendale-Apartments.d901769277689110528-aaApartments.Travel-Guide-Accommodation) - 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[Flights to Lenox](https://www.expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights) - [Flights to Stockbridge](https://www.expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights) - [Flights from Lee](https://www.expedia.ca/lp/flights/8572/flights-from-lee) - [Flights from Lenox](https://www.expedia.ca/lp/flights/8587/flights-from-lenox) - [Visit Great Barrington](https://www.expedia.ca/Great-Barrington.dx110336) - [Lake Mansfield Park](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction) - [National Shrine of the Divine Mercy](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Naumkeag Museum](https://www.expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Norman Rockwell Museum](https://www.expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Visit South Lee](https://www.expedia.ca/South-Lee.dx183343) - [Visit Stockbridge](https://www.expedia.ca/Stockbridge.dx162575) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Lenox](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Stockbridge](https://www.expedia.ca/Avis-Car-Rentals-In-Stockbridge.d162575-c41.Car-Rental-Guide-Suppliers) - [Car rental Lee](https://www.expedia.ca/Car-Rentals-In-Lee.d8572.Car-Rental-Guide) - [Car rental Lenox](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide) - [Car rental Stockbridge](https://www.expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)