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) --- --- ## Plan a trip to see Chesterwood Price found within the past 48 hours. Click for updated prices. ![The White House Inn](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The White House Inn CA $1,117 per person May 6 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 9.2/10 Wonderful! (254 reviews) Room space and set up was not as expected. Reviewed on Feb 6, 2026 ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Equinox Golf Resort & Spa Manchester Village Historic District CA $1,171 per person May 6 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 7.4/10 Good! (567 reviews) We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. Reviewed on Jan 24, 2026 ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View CA $1,134 per person May 6 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 9.4/10 Exceptional! (772 reviews) The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. Reviewed on Jan 28, 2026 ### 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=2026-02-12&endDate=2026-02-13)[Feb 12 - Feb 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-12&endDate=2026-02-13) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-13&endDate=2026-02-14)[Feb 13 - Feb 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=2026-02-13&endDate=2026-02-14) [This 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) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6091841&startDate=20%2F02%2F2026&endDate=22%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) ![Woodland Zen by Avantstay Modern Design + Patio](https://images.trvl-media.com/lodging/106000000/105130000/105129400/105129328/ae66939f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodland Zen by Avantstay Modern Design + Patio 58 Glendale Rd Housatonic MA [](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-Avantstay-Modern-Design-Patio.h105129328.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) [See all 749 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX_POI_Spring_PROMO_6091841)