Title: Chesterwood in South Lee - Tours and Activities | Expedia.ca [Chesterwood Hotels](https://expedia.ca/Chesterwood-Hotels.0-l6091841-0.Travel-Guide-Filter-Hotels)[Flights to South Lee](https://expedia.ca/Cheap-Flights-To-South-Lee.d183343.Travel-Guide-Flights)[Chesterwood Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterwood.d6091841.Car-Rental-Guide)[South Lee Vacation Packages](https://expedia.ca/South-Lee.d183343.Destination-Travel-Guides) # Chesterwood Tours and Activities ## Visit Chesterwood Activities [South Lee travel guide](https://expedia.ca/South-Lee.dx183343) --- --- ### Popular places to visit ![Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking](https://images.trvl-media.com/place/162575/c9de4f96-7bf3-4163-b4b9-feb67c2d801a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Norman Rockwell Museum You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area. [](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) ![A relatively easy hike for this nice view. ](https://images.trvl-media.com/place/110336/0c19841e-0721-43a5-9e62-24d1eb025fa9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Monument Mountain Reservation You can take time to visit Monument Mountain Reservation during your travels to Great Barrington. While you're here, you can savor the top-notch restaurants. [](https://expedia.ca/Monument-Mountain-Reservation-Great-Barrington.d974580971445694464.Vacation-Attraction) ![The mount and historic gardens in lenox massachusetts](https://images.trvl-media.com/place/553248621532665265/8e0a1dfc-df59-49e8-82eb-70a273e3ab05.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### The Mount You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside. [](https://expedia.ca/The-Mount-Lenox.d553248621532665265.Vacation-Attraction) ![A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip](https://images.trvl-media.com/place/8587/1d179a1d-9e13-488f-a60c-fca476ac4122.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tanglewood Music Center 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. [](https://expedia.ca/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction) #### 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. [](https://expedia.ca/Berkshire-Botanical-Garden-West-Stockbridge.d553248621532665247.Vacation-Attraction) #### Mission House You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area. [](https://expedia.ca/Mission-House-Stockbridge.d553248621560941222.Vacation-Attraction) --- ## Best Lodging Options Near Chesterwood ## Check availability on hotels close to Chesterwood [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-08&endDate=2026-02-09) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) ![Classic Stockbridge Cottage](https://images.trvl-media.com/lodging/93000000/92790000/92783800/92783792/3e585a3a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Classic Stockbridge Cottage Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-Berkshire-Cottage-Escape.h92783792.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?impolicy=resizecrop&rw=340&ch=150) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 26 Glendale Road, RR 183 Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Red Lion Inn 30 Main Street Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home](https://images.trvl-media.com/lodging/120000000/120000000/119992800/119992721/d2ba1c67_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home West Stockbridge MA [](https://expedia.ca/Housatonic-Hotels-Modern-Log-Cabin-With-Saltwater-Pool-Mountain-Views-By-Evergreen-Home.h119992721.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?impolicy=resizecrop&rw=340&ch=150) ### Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-Charming-Cape-Cod-Home-In-Prime-Berkshire-Location-5-Minutes-To-Tanglewood.h102001430.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?impolicy=resizecrop&rw=340&ch=150) ### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10 Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.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?impolicy=resizecrop&rw=340&ch=150) ### Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay Stockbridge MA [](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information) ![Stockbridge Home, Come Experience The Berkshires!](https://images.trvl-media.com/lodging/88000000/87640000/87633700/87633659/b5ee0956_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stockbridge Home, Come Experience The Berkshires! Stockbridge MA [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Home.h87633659.Hotel-Information) ![Large Mountaintop Retreat in the Berkshires](https://images.trvl-media.com/lodging/73000000/72370000/72363800/72363795/99395e3a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Large Mountaintop Retreat in the Berkshires West Stockbridge MA [](https://expedia.ca/West-Stockbridge-Hotels-Secluded-Mountaintop-Retreat-In-The-Heart-Of-The-Berkshires.h72363795.Hotel-Information) [See all 746 properties in Chesterwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6091841) 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.