Find hotels near Chesterwood, South Lee from AED 244

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Check prices for these dates

Tonight
10 Apr - 11 Apr
Tomorrow
11 Apr - 12 Apr
This weekend
11 Apr - 13 Apr
Next weekend
18 Apr - 20 Apr

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Compare 713 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
20 Apr - 21 Apr
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
11 Apr - 12 Apr
Tanglewood Suites
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 731
AED 816 total
includes taxes & fees
20 Apr - 21 Apr
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, (123)
"Fantastic in every way! We highly recommend the inn for the warm atmosphere, superb service and lovely facilities. First rate!"
The price is AED 915
AED 1,022 total
includes taxes & fees
11 Apr - 12 Apr
Devonfield Inn B&B
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (409)
"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 Apr - 14 Apr
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 1,441
AED 1,610 total
includes taxes & fees
13 Apr - 14 Apr
33 Main
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"The staff was absolutely amazing, very accommodating and friendly. Overall we had a wonderful experience!! "
The price is AED 393
AED 604 total
includes taxes & fees
30 Apr - 1 May
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
13 Apr - 14 Apr
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, (694)
"Great all around!"
The price is AED 529
AED 591 total
includes taxes & fees
13 Apr - 14 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"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 AED 682
AED 761 total
includes taxes & fees
14 Apr - 15 Apr
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, (616)
"Condo built in 90's - good condition. Didn't know unit was two floors with spiral staircase - we are in our 60's so that wasn't great. "
The price is AED 393
AED 491 total
includes taxes & fees
28 Apr - 29 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Little Lion
Aerial view

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (479)
"A cozy little inn! I recommend it! "
The price is AED 281
AED 314 total
includes taxes & fees
23 Apr - 24 Apr
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 459
AED 512 total
includes taxes & fees
23 Apr - 24 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, (1001)
"Great customer service. Greeted me right away and were very friendly."
The price is AED 340
AED 380 total
includes taxes & fees
16 Apr - 17 Apr
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, (708)
"Manager (owner?) was friendly and helpful. Room was clean and spacious (had corner room). Very good for price. Some annoying ticking sound maybe from room heater throughout the night but otherwise no issues at all. Would stay here again."
The price is AED 244
AED 273 total
includes taxes & fees
13 Apr - 14 Apr
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, (608)
"Staff was very nice and the room was clean and quiet. "
The price is AED 455
AED 509 total
includes taxes & fees
1 May - 2 May
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, (552)
"Perfect spot to spend the weekend visiting my daughter at boarding school!! "
The price is AED 529
AED 591 total
includes taxes & fees
28 Apr - 29 Apr
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"This is my favorite place to stay in Lee! The room is cozy and the complimentary breakfast is delicious! The staff are professional and courteous. I will be back."
The price is AED 455
AED 652 total
includes taxes & fees
14 Apr - 15 Apr
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (546)
"Very nice "
The price is AED 355
AED 397 total
includes taxes & fees
23 Apr - 24 Apr
Berkshires Untold
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (83)
"The Inn was welcoming and comfortable with homemade cookies waiting for us at check in! The decor was especially inviting, we loved it! The staff that took our breakfast order, was equally warm, inviting, and accommodating. "
The price is AED 547
AED 591 total
includes taxes & fees
13 Apr - 14 Apr
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.