Find hotels near Chesterwood, West Stockbridge from ￥10,331

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May 10 - May 11
Tomorrow
May 11 - May 12
This weekend
May 10 - May 12

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Compare 696 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is ￥20,974
￥24,599 total
includes taxes & fees
May 14 - May 15
Lakehouse Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is ￥37,162
￥41,509 total
includes taxes & fees
May 19 - May 20
Chambery Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Cozy, comfortable, feels like you are staying at someone’s home that you love, but, lol with privacy! Breakfast is fabulous and eggs are made to order!"
The price is ￥28,274
￥32,515 total
includes taxes & fees
May 29 - May 30
Blackberry River Inn
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Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (381)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is ￥21,288
￥23,354 total
includes taxes & fees
May 13 - May 14
Shaker Mill Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"This is a charming and very pleasant place to stay."
The price is ￥24,298
￥27,140 total
includes taxes & fees
May 15 - May 16
Brook Farm Inn
Exterior
Race Brook Lodge
2.0 star property
9.4 out of 10, Exceptional, (8)
"It was quiet setting by the rooms are run down "
The price is ￥19,824
￥22,143 total
includes taxes & fees
May 22 - May 23
Race Brook Lodge
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (233)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
The price is ￥15,422
￥17,226 total
includes taxes & fees
May 20 - May 21
Life House Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (507)
"Beautiful location, property in very good condition, clean. "
The price is ￥27,809
￥31,062 total
includes taxes & fees
May 30 - May 31
Courtyard by Marriott Lenox Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (645)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is ￥26,256
￥29,328 total
includes taxes & fees
May 27 - May 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Even though it’s an older hotel I would definitely stay here again because of the service and location. Well appointed rooms and nice small lake area and common areas. The staff were so helpful and friendly- even found us a great place to walk!"
The price is ￥15,715
￥17,553 total
includes taxes & fees
May 22 - May 23
The Black Swan Lee - Lenox, Ascend Hotel Collection
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (463)
"Very clean and commodious. It felt like a home away from home. It might feel dated to some but we found it very luxurious for the price. We didn’t really take advantage of many of the amenities but they are ample. The kitchen was well stocked with everything needed. I would definitely come back."
The price is ￥21,595
￥25,675 total
includes taxes & fees
May 14 - May 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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, (590)
"Great overnight stay. Cleanest place ever. "
The price is ￥10,331
￥11,540 total
includes taxes & fees
May 14 - May 15
Monument Mountain Motel
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (321)
"Great B&B … everything is easy, clean, friendly owners, great breakfast! "
The price is ￥16,313
￥18,760 total
includes taxes & fees
May 12 - May 13
Locust Tree Bed and Breakfast LLC
Seasonal outdoor pool
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (8)
"Booked a weekend stay at Little Cat Lodge for a girlfriends trip. The lodge was very cute and had just about everything we needed. Complimentary breakfast was also much appreciated. 3 women shared a 2-bed bedroom and it was great for size- we loved our little balcony. Would definitely recommend this spot! "
The price is ￥30,761
￥33,221 total
includes taxes & fees
May 12 - May 13
Little Cat Lodge
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (880)
"Nice renovated and updated room in the maple glen building. "
The price is ￥21,653
￥27,666 total
includes taxes & fees
May 21 - May 22
The Red Lion Inn
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"It was a great place to stay for the night. "
The price is ￥18,954
￥22,231 total
includes taxes & fees
May 12 - May 13
The Cornell Inn, Lenox
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (496)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is ￥21,875
￥24,435 total
includes taxes & fees
May 22 - May 23
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (384)
"We loved this place. It's dog friendly, the place is clean and quiet. The proprietor is awesome. It's super friendly. We spent a total of 9 days here, and I'd definitely come back again. Thanks for a great stay"
The price is ￥17,090
￥19,090 total
includes taxes & fees
May 12 - May 13
The Briarcliff Motel
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (110)
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (193)
"safe, clean, perfect location. Communicative hosts who ensured that someone would be on location when I arrived late. Continental breakfast was extensive and healthy. Will definitely be visiting again. "
The price is ￥14,251
￥15,919 total
includes taxes & fees
May 14 - May 15
The Lenox Collection
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See all available properties in Chesterwood
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.

Chesterwood hotels information

Number of reviews
7,371
Accommodation
696 hotels
Lowest Price
￥10,331
Highest Price
￥37,162

Hotels near Other West Stockbridge Attractions

Image for Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(193 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

See properties
Norman Rockwell Museum

Frequently asked questions

What's the area like around Chesterwood?

Chesterwood is located in a scenic area of West Stockbridge known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, check out the 7 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 (0.7 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 7 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.

Recent reviews of Chesterwood hotels
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Nice renovated and updated room in the maple glen building. "
A verified traveler from Norwich stayed at The Red Lion Inn
Posted 6 days ago
The Red Lion Inn