Title: The 10 Best Hotels Near Chesterwood, South Lee | 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 [Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-02-02&endDate=2026-02-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Chesterwood Hotel Reviews ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions](https://images.trvl-media.com/lodging/103000000/102010000/102001500/102001430/b9eabd0d_y.jpg) ### Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions 10/10 Excellent "This is a really lovely, well-kept house. The layout is wonderful, offering plenty of space for everyone to spread out, while also having ample room for spending time all together. There is so much attention to detail (like delicious treats for us on the dining table!), well-stocked kitchen and bathrooms, and plenty of comfortable seating. The host was so nice and extremely responsive each time I reached out. We loved this house and would definitely stay again!" [](https://expedia.ca/Stockbridge-Hotels-Charming-Cape-Cod-Home-In-Prime-Berkshire-Location-5-Minutes-To-Tanglewood.h102001430.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great overnights stay, wish I was here longer " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Walk into town, soak up sun on enclosed porch & steps away from nature trails!](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238_y.jpg) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! 10/10 Excellent "This is one of the most welcoming homes I have ever booked! The host Julie has gone above and beyond to make sure her guests are comfortable and happy in her home! I will definitely book here again!" [](https://expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay](https://images.trvl-media.com/lodging/106000000/105020000/105019600/105019545/a7b5f2d0_y.jpg) ### Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay 10/10 Excellent "Great property and very responsive host" [](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information) ![Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://images.trvl-media.com/lodging/93000000/92110000/92100700/92100621/369ddb1e_y.jpg) ### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10 10/10 Excellent "We had a great time at the Taggart River House! Views and light were unbelievable and it was so nice to be there with extended family and have everyone have their own lovely spaces with bathrooms. A quick walk into town made the days even richer. Would 100% stay again! Also well stocked for kids with a high chair, crib, etc. only missing one stair gate which would have made it perfect, but we put furniture in front of those stairs and that was a great solution too. " [](https://expedia.ca/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.Hotel-Information) ![A Grand property in Historic Stockbridge](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7_y.jpg) ### A Grand property in Historic Stockbridge 10/10 Excellent "Great stay!" [](https://expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) ![Stockbridge Home, Come Experience The Berkshires!](https://images.trvl-media.com/lodging/88000000/87640000/87633700/87633659/b5ee0956_y.jpg) ### Stockbridge Home, Come Experience The Berkshires! 10/10 Excellent "Fully equipped. Pet friendly" [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Home.h87633659.Hotel-Information) ![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 10/10 Excellent "It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!" [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ## Hotels near other Chesterwood attractions ### Norman Rockwell Museum 4.7/5 (252 reviews) You can spend time 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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