Find hotels near Chesterwood, South Lee from SAR 239

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Check prices for these dates

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3 Rab. I - 4 Rab. I
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4 Rab. I - 5 Rab. I
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7 Rab. I - 9 Rab. I
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14 Rab. I - 16 Rab. I

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Compare 711 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

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

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,592
SAR 1,925 total
includes taxes & fees
4 Mar - 5 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 821
SAR 821 total
includes taxes & fees
4 Mar - 5 Mar
Tanglewood Suites
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is SAR 934
SAR 1,043 total
includes taxes & fees
4 Mar - 5 Mar
Devonfield Inn B&B
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (408)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is SAR 544
SAR 597 total
includes taxes & fees
9 Mar - 10 Mar
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is SAR 713
SAR 796 total
includes taxes & fees
4 Mar - 5 Mar
Chambery Inn
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet. "
The price is SAR 516
SAR 744 total
includes taxes & fees
3 Apr - 4 Apr
The Red Lion Inn
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (150)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is SAR 718
SAR 802 total
includes taxes & fees
4 Mar - 5 Mar
Brook Farm Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (606)
"We stayed for a ski trip. The amenities were perfect for our family and friends. "
The price is SAR 446
SAR 551 total
includes taxes & fees
4 Mar - 5 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (475)
"Enjoyed it alot"
The price is SAR 239
SAR 267 total
includes taxes & fees
16 Mar - 17 Mar
The Little Lion
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (689)
"Staff was friendly and accommodating. No issues - hotel and room were clean and well maintained. Would recommend to others."
The price is SAR 540
SAR 603 total
includes taxes & fees
31 Mar - 1 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (23)
"Very nice layout for family. Great coffee and nice bathroom. Updated and modern. "
The price is SAR 491
SAR 549 total
includes taxes & fees
3 Apr - 4 Apr
East Rock Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Some aspects were great, some not. The hotel restruant is an Indian cuisine which we do not like. The room we stayed in has wall and floor structural problems. There was also a camera pin hole in the ceiling over the tub I stuffed a tissue into. It was noisy between 10 to 11 pm as a group of loud drunks were walking down the hall."
The price is SAR 402
SAR 449 total
includes taxes & fees
6 Mar - 7 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
Monument Mountain Motel
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (702)
"Small but clean. Good mattress. Very reasonable price"
The price is SAR 249
SAR 279 total
includes taxes & fees
4 Mar - 5 Mar
Monument Mountain Motel
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (603)
"Small pool and even smaller hot tub. The ceiling above the pool was cracked and sagging in the middle."
The price is SAR 458
SAR 511 total
includes taxes & fees
9 Mar - 10 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (548)
"Great property close to shopping and very clean. "
The price is SAR 476
SAR 532 total
includes taxes & fees
18 Mar - 19 Mar
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox
Front of property

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1002)
"The weather played a part - our room was accessed by a set of outside stairs, and the weather was cold enough to make them a bit perilous. The staff did its best to attend to it."
The price is SAR 353
SAR 540 total
includes taxes & fees
24 Mar - 25 Mar
The Cornell Inn, Lenox
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (513)
"The restaurant and lounge area is so inviting, and staff is all around excellent."
The price is SAR 363
SAR 405 total
includes taxes & fees
16 Mar - 17 Mar
Life House Berkshires
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is SAR 371
SAR 401 total
includes taxes & fees
6 Mar - 7 Mar
Inn at Silver Maple Farm
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (433)
"Our one night at The Constance recently (February 2025), was fantastic! The inn is warm and welcoming, spotlessly clean, and beautifully decorated with lots of vintage charm and all the comfy, modern conveniences one would expect. We absolutely loved it! Each staff member we had contact with (Logan, Brenda and Stacy) was professional and friendly. Communication was efficient and timely. As we were in Lenox off-season, the inn was exceptionally quiet, with only two other rooms booked during...
The price is SAR 390
SAR 435 total
includes taxes & fees
4 Mar - 5 Mar
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (16)
"Room was very cozy and beautiful. Brad was very helpful and pleasant. The breakfast was delicious. We had a great getaway. Thank you. "
The price is SAR 556
SAR 621 total
includes taxes & fees
9 Mar - 10 Mar
Wilder House Berkshires
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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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 8 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. Other good choices within a few miles include The Red Lion Inn and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG.

How many hotels are there close to Chesterwood?

Expedia has 8 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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.