10 Best Hotels & Accommodation Closest to Chesterwood in South Lee from AU$177

Our top choices for Chesterwood hotels

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

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

0.6 km from Chesterwood

Philippe

includes taxes & fees

4 Aug - 5 Aug

2. Monument Mountain Motel

8.7 km from Chesterwood

Yekaterina

includes taxes & fees

26 July - 27 July

Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

3. East Rock Inn

10.1 km from Chesterwood

Eleanor

includes taxes & fees

5 Aug - 6 Aug

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

8 km from Chesterwood

Kathleen

includes taxes & fees

16 Aug - 17 Aug

5. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

6.6 km from Chesterwood

Kimberly

includes taxes & fees

27 July - 28 July

6. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Michelle

includes taxes & fees

5 Aug - 6 Aug

7. The Little Lion

5.1 km from Chesterwood

Mia

includes taxes & fees

27 July - 28 July

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8.6 km from Chesterwood

Lisa

includes taxes & fees

20 Aug - 21 Aug

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

9. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Andrew

includes taxes & fees

29 July - 30 July

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

10. The Yankee Inn

14.9 km from Chesterwood

Michael

includes taxes & fees

23 July - 24 July

11. Berkshires Untold

13 km from Chesterwood

Debra

includes taxes & fees

29 July - 30 July

12. Chambery Inn

8.7 km from Chesterwood

Joseph

includes taxes & fees

27 July - 28 July

13. Berkshire Lake Lodge

16.2 km from Chesterwood

Grzegorz

includes taxes & fees

30 July - 31 July

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

15.5 km from Chesterwood

Courtney

includes taxes & fees

26 July - 27 July

15. Devonfield Inn B&B

7.5 km from Chesterwood

Francis

includes taxes & fees

26 July - 27 July

16. Quality Inn Great Barrington

10.3 km from Chesterwood

Lynn

includes taxes & fees

27 July - 28 July

17. Berkshire Mountain Lodge

15.9 km from Chesterwood

Joseph

includes taxes & fees

4 Aug - 5 Aug

Desk, laptop workspace, iron/ironing board (on request), free WiFi

18. Granville House

6.4 km from Chesterwood

Nicole

includes taxes & fees

29 July - 30 July

19. Shaker Mill Inn

5.8 km from Chesterwood

Mervin

includes taxes & fees

27 July - 28 July

20. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Izabela

includes taxes & fees

29 July - 30 July

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 113 reviews	View
Monument Mountain Motel	2.5 star property	9.0 Wonderful 885 reviews	View
East Rock Inn	2.0 star property	9.6 Exceptional 51 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	2.5 star property	8.8 Excellent 793 reviews	View
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG	3.5 star property	9.2 Wonderful 941 reviews	View

Top Chesterwood Hotel Reviews

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"Tom was a great host. Easy to communicate and just a nice guy. The property was in a great location close to all the places we went to-Tanglewood, Norman Rockwell Museum, Botanical Gardens, Lenox, Stockbridge and more. Home was very spacious with a great outdoor deck. Nice grill that we used several times. Would definitely stay there again."

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

8/10 Good

"This house is magnificent but unfortunately is not maintained well. The basement bedroom had not been cleaned and had spiders. The shower was so dirty that we did not use it. The picture of the deck has an umbrella for shade. No umbrella and the furniture cover was upside down on the deck full of stagnant water. The photos of the garden were deceiving as the raised beds were full of weeds and the lawn has not been mowed for a long time. There were strict instructions for taking out the trash but could not be followed as the trash had not been picked up from the previous tenant. We paid a lot of money to rent this house and don't feel that it lived up to its description."

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

10/10 Excellent

"Large comfortable house, in a beautiful location with a large grassy back yard, and right next to a lovely church. Plus totally central to the village of Stockbridge and to trails going along the Housatonic River and up into a state forrest. Loved it"

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10/10 Excellent

"This house was such a perfect place for a family getaway/ it was spacious, clean, well- equipped and comfortable. The property setting is stunning and had so many small touches that added up to a great rental. Quick and responsive communication/ and location was very convenient to other Berkshires destinations such stores, museums and Tanglewood. Highly Recommended!!!!!"

Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway

10/10 Excellent

"We had a very comfortable and relaxed stay. 3 real bedrooms and 2 bathrooms! Emily was a super responsive host whenever I had a question. Great location that allowed us to do everything we wanted to do very easily."

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"What a gem! That house is the best supplied house I’ve been in. Everything you could want was there. The large backyard was spectacular surrounded by a forest. The house was clean, the kitchen well equipped. Its location was walking distance to the Norman Rockwell museum, the Berkshire botanical garden, and Chesterwood. It was a short drive to Tanglewood, the Mahaiwe, and Jacob‘s pillow. The week was too short."

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

10/10 Excellent

"Great modern home, well stocked. The home is not huge, but with 2 living areas, a screened in porch and a large kitchen, we had plenty of room to stretch out.Although on a main road, the house was set back and felt totally private. The location was incredibly convenient, with quick drives to Great Barrington, Stockbridge and Lennox, as well as Norman Rockwell Museum, Botanical Gardens, Chesterwood, Tanglewood. Berkshire Mt Bakery and the Common are terrific and just 2 minutes away.A few minor things could be improved - shower could use an adjustable head so you don't have to stand in the drain depression, some cookware is ready for an upgrade. But very minor. Would stay again."

Stockbridge Retreat w/ Pool & Hot Tub!

10/10 Excellent

"We had such a nice, relaxing visit to the Berkshires! The house is in a great location to visit lots of sights, but you could also just stay and enjoy the pool and hot tub. We loved sitting on the screened porch. There was also room for everyone to spread out inside (with multiple TVs and good WiFi) or to come together in the big family room. Our daughter enjoyed playing the piano. The kitchen is super well-equipped. There are 2 primary bedroom suites, which is very handy. The house was very clean. The host was very responsive and helpful. Only small glitch was we were given a wrong/old combination to the lockbox with the door key but that was quickly sorted out. All in all, a great place."

Hotels near other Chesterwood attractions

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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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 10 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 10 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.

Top Hotels Near Chesterwood in South Lee from AU$177

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Our top choices for Chesterwood hotels

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

2. Monument Mountain Motel

3. East Rock Inn

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

5. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

6. Quality Inn Lee - Lenox South

7. The Little Lion

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

9. Best Western Plus Berkshire Hills Inn & Suites

10. The Yankee Inn

11. Berkshires Untold

12. Chambery Inn

13. Berkshire Lake Lodge

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

15. Devonfield Inn B&B

16. Quality Inn Great Barrington

17. Berkshire Mountain Lodge

18. Granville House

19. Shaker Mill Inn

20. Element by Marriott Lenox Berkshires

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

Secluded Family Home in Serene Stockbridge Woods

Hotels near other Chesterwood attractions

Norman Rockwell Museum

Frequently asked questions