The Best Hotels Closest to Chesterwood in South Lee for 2026

Our top choices for Chesterwood hotels

Suite, Private Bathroom (RedBird Suite) | View from room

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

0.6 km from Chesterwood

Deborah

SAR 1,499 total

includes taxes & fees

29 Jun - 30 Jun

The Red Lion Inn

3.3 km from Chesterwood

molly

SAR 805 total

includes taxes & fees

22 Jun - 23 Jun

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8.6 km from Chesterwood

Helena

SAR 780 total

includes taxes & fees

21 Jun - 22 Jun

Prospect Berkshires

12.8 km from Chesterwood

Conor

SAR 1,503 total

includes taxes & fees

15 Jun - 16 Jun

Classic Double Room, 2 Queen Beds, Courtyard View | Bathroom | Designer toiletries, hair dryer, towels, soap

East Rock Inn

10.1 km from Chesterwood

Laura

SAR 604 total

includes taxes & fees

17 Jun - 18 Jun

The Cornell Inn, Lenox & The Berkshires

10.7 km from Chesterwood

Arthur

SAR 699 total

includes taxes & fees

15 Jun - 16 Jun

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8 km from Chesterwood

Kathleen

SAR 574 total

includes taxes & fees

23 Jun - 24 Jun

Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Nancy

SAR 709 total

includes taxes & fees

29 Jun - 30 Jun

Inn at Silver Maple Farm

17.5 km from Chesterwood

Erdem

SAR 668 total

includes taxes & fees

17 Jun - 18 Jun

Little Cat Lodge

16.3 km from Chesterwood

Jason

SAR 639 total

includes taxes & fees

15 Jun - 16 Jun

The Whitlock

9.8 km from Chesterwood

Linda

SAR 792 total

includes taxes & fees

18 Jun - 19 Jun

Berkshires Untold

13 km from Chesterwood

Carin

SAR 570 total

includes taxes & fees

18 Jun - 19 Jun

Quality Inn Great Barrington

10.3 km from Chesterwood

Braynd

SAR 394 total

includes taxes & fees

17 Jun - 18 Jun

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

The Yankee Inn

14.9 km from Chesterwood

Mark

SAR 439 total

includes taxes & fees

15 Jun - 16 Jun

Wilder House Berkshires

19.9 km from Chesterwood

Jennifer

SAR 774 total

includes taxes & fees

22 Jun - 23 Jun

In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

6.2 km from Chesterwood

Heather

SAR 331 total

includes taxes & fees

15 Jun - 16 Jun

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

15.5 km from Chesterwood

Matthew

SAR 587 total

includes taxes & fees

22 Jun - 23 Jun

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Anandaraja

SAR 483 total

includes taxes & fees

17 Jun - 18 Jun

The Central Downtown Inn & Suites

19.6 km from Chesterwood

Aisha

SAR 507 total

includes taxes & fees

29 Jun - 30 Jun

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

robert

SAR 331 total

includes taxes & fees

15 Jun - 16 Jun

View all properties

Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood	4.5 star property	9.2 Wonderful 111 reviews	View
The Red Lion Inn	3.5 star property	8.8 Excellent 1,007 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	3.0 star property	9.4 Exceptional 785 reviews	View
Prospect Berkshires	3.0 star property	9.8 Exceptional 29 reviews	View
East Rock Inn	2.0 star property	9.4 Exceptional 48 reviews	View

Top Chesterwood Hotel Reviews

A Grand property in Historic Stockbridge

10/10 Excellent

"We had a wonderful stay at the Taggart House - what a memorable place! We are five couples who get together every other year and this was the perfect place for us. There are so many things to mention: the feeling of staying in this gracious and historic home; the care with which it has been restored; the ability to accommodate all five couples in lovely, comfortable rooms (with en suites) that pleased us all; the size and usability of the well-stocked kitchen; the gracious dining room that could seat our entire group; the fun (and oft-used) billiards room; the wonderful sun porch that opened up to the beautiful back yard; and the easy proximity to so many of the historic places that the Berkshires has to offer. Well done Caitlin and George!I speak for our group in saying that we would not hesitate to recommend the Taggart House to others planning to visit the area - and we hope to return for another memorable stay."

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"We loved this property! We stayed for a grown-up 'girls weekend' with a group of 7 adults and although this is definitely a family/kid friendly house, it was also great for us! Comfortable rooms and nice functional kitchen, but the real star of the show is the covered back porch - a beautiful and peaceful spot to hang out, enjoy a meal, and do a little birding if that's your thing. While in town we visited the Normal Rockwell Museum, Jiminy Peak Mtn Adventure Park, and Turn Park Art Space - all within a convenient driving distance. The hosts were great with communication, and check-in/out was a breeze! Would stay again!"

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

10/10 Excellent

"Overall a nice property that was as it was listed. The kitchen was well stocked and the open space and windows were really nice. It felt very private. The bed in the master was very comfortable and the air conditioning kept the place nice and cool. My only feedback is that the outside needs some attention. Perhaps we were the first visitors this summer."

Classic Stockbridge Cottage

10/10 Excellent

"Spacious, quiet, comfortable, and well-appointed rental, conveniently located for access to towns and attractions in south Berkshire County. New washer and dryer was a plus, as was the remodeled master bathroom. Owners are very responsive. Would definitely rent again. Thank you!"

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"The property was excellent- great location, cozy, and really well stocked with everything you might need.We had a very rainy weekend, so did lots of cooking, and found all the essentials for fun meals at the house! We will definitely be back!"

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10/10 Excellent

"2 empty nester couples visiting on a rainy weekend. House was exactly as advertised. Beautiful decor & comfortable furnishings. Communication with host excellent. Walkable to village of Stockbridge which was great. Host provided excellent recommendations on local attractions especially valuable on dreary weather. Highly recommend to adults, will return if in area."

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (347 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in 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, check out the 10 hotels and other accommodations you'll find within a mile.

What's the best hotel 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 traveler 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 are there close to Chesterwood?

Expedia has 10 hotels and other accommodations within a mile from Chesterwood.

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

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.

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.

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Our top choices for Chesterwood hotels

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

The Red Lion Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Prospect Berkshires

East Rock Inn

The Cornell Inn, Lenox & The Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Courtyard by Marriott Lenox Berkshires

Inn at Silver Maple Farm

Little Cat Lodge

The Whitlock

Berkshires Untold

Quality Inn Great Barrington

The Yankee Inn

Wilder House Berkshires

Travelodge by Wyndham Great Barrington Berkshires

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

Best Western Plus Berkshire Hills Inn & Suites

The Central Downtown Inn & Suites

Howard Johnson by Wyndham Lenox

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

A Grand property in Historic Stockbridge

Hotels near other Chesterwood attractions

Norman Rockwell Museum

Frequently asked questions

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Other Hotels near Chesterwood, South Lee

More Hotel Options in Chesterwood

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