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A historic square with a statue of a woman holding scales and a sword, surrounded by traditional half-timbered buildings under a twilight sky.

Search Hotels Near Chesterwood, South Lee

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    Check prices for these dates, 12 – 13 December 2026

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    Our top choices for Chesterwood hotels

    1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    A two-story house with a brick entrance and a white facade.

    2. Monument Mountain Motel

    A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

    3. Quality Inn Lee - Lenox South

    A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

    4. The Yankee Inn

    Two Adirondack chairs facing a river with a forested hill in the background.

    5. Berkshires Untold

    A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

    6. Element by Marriott Lenox Berkshires

    A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

    7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

    An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

    8. Courtyard by Marriott Lenox Berkshires

    An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

    9. Berkshire Mountain Lodge

    A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

    10. Hampton Inn & Suites Berkshires-Lenox

    A spacious hotel lobby with multiple seating areas, large windows, and a television.

    11. Chambery Inn

    A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

    12. Brook Farm Inn

    A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

    13. Quality Inn Great Barrington

    A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

    14. East Rock Inn

    A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

    15. Berkshire Lake Lodge

    A calm lake at dusk with a wooden dock and two chairs facing the water.

    16. Hilton Garden Inn Lenox Pittsfield

    A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

    17. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    An indoor swimming pool with clear water, tiled floors, and a blue wall.

    18. Best Western Plus Berkshire Hills Inn & Suites

    A reception area with a wooden reception desk, a seating area with sofas, a colorful stained glass window, a mounted television, and various potted plants.

    19. The Inn at Stockbridge

    Front of property

    20. Howard Johnson by Wyndham Lenox

    A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

    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.

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    Compare top hotels near Chesterwood

    A two-story house with a brick entrance and a white facade.

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    0.4 mi from Chesterwood View

    A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

    Monument Mountain Motel

    5.4 mi from Chesterwood View

    A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

    Quality Inn Lee - Lenox South

    5.7 mi from Chesterwood View

    Two Adirondack chairs facing a river with a forested hill in the background.

    The Yankee Inn

    9.3 mi from Chesterwood View

    A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

    Berkshires Untold

    8.1 mi from Chesterwood View
    9.4Exceptional120 reviews9.0Wonderful944 reviews8.6Excellent1,000 reviews9.2Wonderful1,001 reviews9.0Wonderful1,074 reviews
    £346 includes taxes & fees12 Dec - 13 Dec £50 includes taxes & fees13 Dec - 14 Dec £72 includes taxes & fees6 Dec - 7 Dec £89 includes taxes & fees13 Dec - 14 Dec £89 includes taxes & fees17 Nov - 18 Nov
    • Breakfast included
    • Pool
    • Spa
    • Pet-friendly
    • WiFi included
    • Parking
    • Breakfast included
    • Pool
    • Spa
    • Pet-friendly
    • WiFi included
    • Parking
    • Breakfast included
    • Pool
    • Spa
    • Pet-friendly
    • WiFi included
    • Parking
    • Breakfast included
    • Pool
    • Spa
    • Pet-friendly
    • WiFi included
    • Parking
    • Breakfast included
    • Pool
    • Spa
    • Pet-friendly
    • WiFi included
    • Parking

    Other attractions near Chesterwood

    Norman Rockwell Museum

    Rating: 9.4/10 (347 reviews)

    You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

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    Berkshire Botanical Garden

    Rating: 9.4/10 (14 reviews)

    Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.

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    Mission House

    Rating: 9.6/10 (5 reviews)

    You can spend time studying the exhibits at Mission House in Stockbridge. Wander the lakeside in this quaint area.

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    Naumkeag Museum

    Rating: 9.4/10 (10 reviews)

    You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.

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    National Shrine of the Divine Mercy

    Rating: 9.0/10 (83 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.

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    Schantz Galleries

    Rating: 7.2/10 (5 reviews)

    You can spend an afternoon studying the exhibits at Schantz Galleries during your travels in Stockbridge. Wander the lakeside in this quaint area.

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    Art et Industrie

    Rating: 8.0/10 (5 reviews)

    You can spend an afternoon exploring the galleries in Art et Industrie during your trip to Great Barrington. Amble around this quaint area's gardens or seek out the hiking trails.

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    Berkshire Theatre Festival

    Rating: 8.8/10 (3 reviews)

    You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.

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    Top Chesterwood Hotel Reviews

    Granville House

    A dining table with pastries, a coffee pot, and a vase of sunflowers.

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn".

    The Inn at Stockbridge

    Front of property

    Brook Farm Inn

    A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

    Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

    A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

    The Black Swan Lee - Lenox, an Ascend Collection Hotel

    A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

    The Cornell Inn, Lenox & The Berkshires

    A snow-covered outdoor area with a patio, seating, and a covered dining area.

    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, take a look at the 11 hotels and other accommodation options you'll find within a mile.

    Where is the best place to stay close to Chesterwood?

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveller 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. Another good choice is The Red Lion Inn, located 2.1 mi (3.3 km) away.

    How many hotels will I find near Chesterwood?

    Expedia has 11 hotels and other accommodation options within a mile from Chesterwood.

    If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

    Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

    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 Lenox Arts Center while you're out sightseeing near Chesterwood.