The Best Hotels Closest to Chesterwood in South Lee - 2026 Updated Prices

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Our top choices for Chesterwood hotels

Grand Villa, 3 Bedrooms | Iron/ironing board, free cots/infant beds, WiFi, bed sheets

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

6.7 km from Chesterwood

Linda

₹9,695

₹12,677 total

includes taxes & fees

14 Sept - 15 Sept

Comfort Double Room, Lake View | Desk, laptop workspace, free WiFi

2. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

₹13,267

₹14,819 total

includes taxes & fees

8 Sept - 9 Sept

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

42-inch flat-screen TV with cable channels, TV

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

3. The Yankee Inn

14.9 km from Chesterwood

Karen

₹10,961

₹12,244 total

includes taxes & fees

22 Sept - 23 Sept

4. Berkshire Mountain Lodge

15.9 km from Chesterwood

Robert

₹7,522

₹10,513 total

includes taxes & fees

1 Oct - 2 Oct

Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

5. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Nancy

₹12,397

₹13,848 total

includes taxes & fees

13 Sept - 14 Sept

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout curtains

6. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Prasanna

₹8,496

₹9,490 total

includes taxes & fees

9 Sept - 10 Sept

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

8 km from Chesterwood

BJORN

₹12,473

₹13,932 total

includes taxes & fees

15 Sept - 16 Sept

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board (on request)

8. The Little Lion

5.1 km from Chesterwood

Anne

₹10,630

₹11,874 total

includes taxes & fees

9 Sept - 10 Sept

Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cots/infant beds, rollaway beds

9. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Christine

₹9,558

₹10,676 total

includes taxes & fees

27 Sept - 28 Sept

10. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Lawrence

₹18,426

₹20,582 total

includes taxes & fees

13 Sept - 14 Sept

Deluxe Suite, Private Bathroom (Clark - Pets Allowed)

Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)

Standard Apartment, Private Bathroom (Greylock - No Pets)

11. Shaker Mill Inn

5.8 km from Chesterwood

Mervin

₹13,657

₹14,982 total

includes taxes & fees

8 Sept - 9 Sept

Basic Double Room | Blackout curtains, iron/ironing board (on request), free WiFi

12. Sunset Inn

9.1 km from Chesterwood

Joann

₹8,501

₹9,496 total

includes taxes & fees

8 Sept - 9 Sept

The Fox Den in the Mainhouse | 1 bedroom, premium bedding, laptop workspace, iron/ironing board

13. The Inn at Stockbridge

5.2 km from Chesterwood

Jodi

₹35,622

₹41,780 total

includes taxes & fees

13 Sept - 14 Sept

Deluxe Suite | Iron/ironing board, free WiFi, individually decorated

14. Chambery Inn

8.7 km from Chesterwood

Alexandra

₹25,513

₹28,498 total

includes taxes & fees

7 Sept - 8 Sept

Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board (on request), free WiFi, bed sheets

15. Brook Farm Inn

9.1 km from Chesterwood

Carrie

₹23,770

₹27,306 total

includes taxes & fees

17 Sept - 18 Sept

16. Little Cat Lodge

16.3 km from Chesterwood

Kees

₹16,924

₹18,955 total

includes taxes & fees

7 Sept - 8 Sept

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

15.5 km from Chesterwood

Steve

₹11,150

₹12,455 total

includes taxes & fees

9 Sept - 10 Sept

18. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Tracy

₹16,787

₹18,751 total

includes taxes & fees

9 Sept - 10 Sept

19. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

₹13,823

₹15,440 total

includes taxes & fees

10 Sept - 11 Sept

50-inch flat-screen TV with cable channels, TV, streaming services

Deluxe Double Suite- NO PETS ALLOWED | Iron/ironing board, cots/infant beds, rollaway beds, free WiFi

20. The Central Downtown Inn & Suites

19.6 km from Chesterwood

Rena

₹9,355

₹10,449 total

includes taxes & fees

13 Sept - 14 Sept

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Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

The Little Lion

10/10 Excellent

"Easy check in. The rooms were clean. Beds comfy."

The Inn at Stockbridge

10/10 Excellent

"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"

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

10/10 Excellent

"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."

Other attractions near Chesterwood

Norman Rockwell Museum

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

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

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

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

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

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

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

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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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.

Search Hotels Near Chesterwood, South Lee

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Our top choices for Chesterwood hotels

1. Holiday Inn Club Vacations Oak 'n Spruce Resort

2. Berkshire Lake Lodge

3. The Yankee Inn

4. Berkshire Mountain Lodge

5. Hampton Inn & Suites Berkshires-Lenox

6. Best Western Plus Berkshire Hills Inn & Suites

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

8. The Little Lion

9. Quality Inn Lee - Lenox South

10. Element by Marriott Lenox Berkshires

11. Shaker Mill Inn

12. Sunset Inn

13. The Inn at Stockbridge

14. Chambery Inn

15. Brook Farm Inn

16. Little Cat Lodge

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

18. Courtyard by Marriott Lenox Berkshires

19. Hilton Garden Inn Lenox Pittsfield

20. The Central Downtown Inn & Suites

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Little Lion

The Inn at Stockbridge

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

Other attractions near Chesterwood

Norman Rockwell Museum

Berkshire Botanical Garden

Mission House

Naumkeag Museum

National Shrine of the Divine Mercy

Schantz Galleries

Art et Industrie

Berkshire Theatre Festival

Frequently asked questions

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