Top Hotels Near Chesterwood in West Stockbridge from AU$106

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May 13 - May 14
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May 14 - May 15
This weekend
May 17 - May 19
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May 24 - May 26

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Accommodation near Chesterwood

Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1005)
"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 AU$171
per night
21 May - 22 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (881)
"."
The price is AU$236
per night
21 May - 22 May
The Red Lion Inn
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (237)
"Dinner was amazing and the staff very courteous "
The price is AU$167
per night
21 May - 22 May
Life House Berkshires
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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, (464)
"Great location. Shopping resorts restaurants"
The price is AU$235
per night
21 May - 22 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (508)
"Beautiful location, property in very good condition, clean. "
The price is AU$257
per night
30 May - 31 May
Courtyard by Marriott Lenox Berkshires
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 AU$240
per night
15 May - 16 May
Lakehouse Inn
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (647)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is AU$257
per night
27 May - 28 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 AU$213
per night
10 June - 11 June
The Cornell Inn, Lenox
Room, 1 Queen Bed, Non Smoking
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (590)
"Great overnight stay. Cleanest place ever. "
The price is AU$112
per night
22 May - 23 May
Monument Mountain Motel
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, (212)
"Absolutely gorgeous room. Wonderful staff, I felt like royalty. "
The price is AU$235
per night
23 May - 24 May
Apple Tree Inn
Standard Room, 2 Queen Beds, Non Smoking
Quality Inn
2.5 star property
8.0 out of 10, Very good, (1005)
"Whenever we are in the area we have stayed and been pleased. "
The price is AU$135
per night
22 May - 23 May
Quality Inn
Standard Room
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (497)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is AU$238
per night
22 May - 23 May
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is AU$421
per night
21 May - 22 May
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 AU$310
per night
9 June - 10 June
Blackberry River Inn
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (455)
" price, close to everything, "
The price is AU$117
per night
22 May - 23 May
Travelodge by Wyndham Great Barrington Berkshires
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 AU$186
per night
21 May - 22 May
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
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (382)
"Perfect little country inn tucked in the Berkshires, convenient to the highway but off the beaten path on a quiet rural road. Our first floor suite was spacious, inviting, comfortable, and clearly designed with care. Would definitely return next time we’re in the area. "
The price is AU$228
per night
15 May - 16 May
Shaker Mill Inn
Standard Room, 1 King Bed
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (502)
"The woman at check-in was kind. We had a lovely view. Place was in a great location with a comfortable bed."
The price is AU$106
per night
21 May - 22 May
Econo Lodge Lee - Great Barrington
Don't see what you're looking for?
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 Travel Info

Number of reviews
9,502
Closest neighbourhood
Richmond
Accommodation
684 hotels
Known landmark
Berkshire Botanical Garden
Mid-Range hotels
Devonfield Inn B&B, The Inn at Stockbridge and 33 Main
Budget hotels
Chambery Inn, The Red Door B&B and The Briarcliff Motel
Location
West Stockbridge, United States of America
Lowest price
AU$106
Highest price
AU$421

Stay close to other popular attractions

Image for Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to 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, take a look at the 7 hotels and other accommodation options you'll find within a mile.

How many hotels will I find near Chesterwood?

Expedia has 7 hotels and other accommodation options within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

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 in Chesterwood
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"."
A verified traveller stayed at The Red Lion Inn
Posted 1 day ago
The Red Lion Inn