Find hotels near Chesterwood, South Lee from AED 229

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Check prices for these dates

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

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Compare 712 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
View from room

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
23 Feb - 24 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
Property grounds

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
23 Feb - 24 Feb
Tanglewood Suites
Granville House
Room

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 918
AED 1,026 total
includes taxes & fees
27 Feb - 28 Feb
Granville House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (407)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
25 Feb - 26 Feb
Shaker Mill Inn
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (247)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is AED 463
AED 543 total
includes taxes & fees
28 Feb - 1 Mar
Lakehouse 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 AED 698
AED 779 total
includes taxes & fees
23 Feb - 24 Feb
Chambery Inn
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"The heated pool . Nice to go outside for a swim when it's 23 degrees outside ."
The price is AED 536
AED 763 total
includes taxes & fees
25 Mar - 26 Mar
The Red Lion Inn
Inn at Kenmore Hall
Front of property

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
23 Feb - 24 Feb
Inn at Kenmore Hall
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 AED 750
AED 837 total
includes taxes & fees
25 Feb - 26 Feb
Brook Farm Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (597)
"Just spent 3 nights. Kids enjoyed all the amenities. Rooms were decent. Staff was friendly. We will be going back. "
The price is AED 437
AED 540 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (473)
"Easy check in. No disturbances. Cute rooms. Disappointed there was no availability for my last trip to GB because I would have loved to stay here one last time. "
The price is AED 229
AED 256 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, (22)
"Everything is brand new and clean!"
The price is AED 453
AED 506 total
includes taxes & fees
25 Mar - 26 Mar
East Rock Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything! "
The price is AED 403
AED 450 total
includes taxes & fees
2 Mar - 3 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (598)
"Had to work for the day at Ski Butternut. Pros: Proximity to mountain and town, clean, friendly & accommodating staff, chargers for EVs, fitness 24/7, Barrington Brewery literally across the street for nice pub fare meal. Cons: none Food: N/A (left for work super early, but it smelled good! lol) Tips: make sure your room doesn't share a wall with the emergency stairs. Rumbles the wall and anything attached. Staff took care of a switch immediately. Would stay again for leisure."
The price is AED 441
AED 492 total
includes taxes & fees
25 Feb - 26 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (700)
"Small but clean. Good mattress. Very reasonable price"
The price is AED 244
AED 273 total
includes taxes & fees
23 Feb - 24 Feb
Monument Mountain Motel
Courtyard by Marriott Lenox Berkshires
Lobby

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 AED 466
AED 521 total
includes taxes & fees
9 Mar - 10 Mar
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Staff were helpful and engaging. The fireplace in the room made it extra comfy. So many delights and surprises made for an excellent experience! "
The price is AED 382
AED 448 total
includes taxes & fees
9 Mar - 10 Mar
The Cornell Inn, Lenox
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is AED 547
AED 591 total
includes taxes & fees
23 Feb - 24 Feb
Inn at Silver Maple Farm
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Exterior

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

3.5 star property
8.6 out of 10, Excellent, (428)
"We stayed at the Constance location which was gorgeous, inside and out. Having never stayed at a bed and breakfast, we weren't too sure what to expect but it was the perfect vibe for the town/trip. This was a great, little New England getaway for a few days. It felt like a Hallmark movie or something. "
The price is AED 383
AED 428 total
includes taxes & fees
25 Feb - 26 Feb
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Apple Tree Inn
Exterior

Apple Tree Inn

3.0 star property
8.4 out of 10, Very Good, (277)
"Friendly, welcoming, accommodating! We will visit again and recommend this place to others."
The price is AED 575
AED 642 total
includes taxes & fees
23 Feb - 24 Feb
Apple Tree Inn
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.

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.