Find hotels near Chesterwood, South Lee from AED 234

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Check prices for these dates

Tonight
11 Mar - 12 Mar
Tomorrow
12 Mar - 13 Mar
This weekend
14 Mar - 16 Mar
Next weekend
21 Mar - 23 Mar

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Compare 708 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 AED 1,559
AED 1,885 total
includes taxes & fees
12 Mar - 13 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 AED 804
AED 804 total
includes taxes & fees
12 Mar - 13 Mar
Tanglewood Suites
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (81)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 826
AED 923 total
includes taxes & fees
18 Mar - 19 Mar
Granville House
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 AED 915
AED 1,021 total
includes taxes & fees
12 Mar - 13 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 AED 533
AED 584 total
includes taxes & fees
13 Mar - 14 Mar
Shaker Mill Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,410
AED 1,575 total
includes taxes & fees
12 Mar - 13 Mar
33 Main
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 AED 698
AED 779 total
includes taxes & fees
12 Mar - 13 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, (1000)
"This is a gem in the Berkshires! It is quaint yet cool. We stayed in winter, so nearby attractions were limited for non-skiers but I'd go again for the heated pool, pub, great rooms and wonderful staff!"
The price is AED 492
AED 714 total
includes taxes & fees
9 Apr - 10 Apr
The Red Lion Inn
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
12 Mar - 13 Mar
Inn at Kenmore Hall
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (691)
"I’ve stayed here a few times with my grandkids. They love the pool and game room. The breakfast is incredibly impressive and the staff is super friendly and helpful. A friend told me about this Marriot and she raved about how her kids loved it. Also, it’s very close to Butternut where we like to ski. All around great spot to stay!"
The price is AED 529
AED 591 total
includes taxes & fees
30 Mar - 31 Mar
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (608)
"2nd time staying i love this resort. I wish i can stay more days "
The price is AED 437
AED 539 total
includes taxes & fees
12 Mar - 13 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 AED 234
AED 262 total
includes taxes & fees
25 Mar - 26 Mar
The Little Lion
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (24)
"The property is well maintained and set back from the road. It was very quiet and the rooms are fantastic. A must stay if you are going to be in the area. "
The price is AED 503
AED 562 total
includes taxes & fees
25 Mar - 26 Mar
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, (1000)
"Great staff, clean comfortable room. Very nice. Breakfast was not good, stale muffins and danish. A little overpriced for what it was."
The price is AED 359
AED 401 total
includes taxes & fees
17 Mar - 18 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
Monument Mountain Motel
Room, 1 Queen Bed, 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, (704)
"I've stayed here many times for both brief stays and full weeks. Never disappointed. Affordable, clean family-run operation. The only place I stay in the Berkshires. "
The price is AED 244
AED 273 total
includes taxes & fees
12 Mar - 13 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, (604)
"Perfect except for not enough seats available during breakfast "
The price is AED 449
AED 502 total
includes taxes & fees
17 Mar - 18 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, (549)
"Great property close to shopping and very clean. "
The price is AED 466
AED 521 total
includes taxes & fees
27 Mar - 28 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, (1000)
"Unique rooms, great breakfast, complimentary apple cider is a treat, friendly staff "
The price is AED 434
AED 628 total
includes taxes & fees
25 Mar - 26 Mar
The Cornell Inn, Lenox
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (521)
" I’ve place , clean, great bar and restaurant "
The price is AED 355
AED 397 total
includes taxes & fees
24 Mar - 25 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 AED 364
AED 393 total
includes taxes & fees
12 Mar - 13 Mar
Inn at Silver Maple Farm
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 Tanglewood Suites.

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.