Hotels near Chesterwood

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Top 10 Hotels Near Chesterwood

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, 1,009 reviews
"The hotel was great! The rooms were clean and well appointed."
The price is RM632
RM706 total
includes taxes & fees
26 Jun - 27 Jun
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, 905 reviews
"Classic hotel but our room was far from main desk and fairly inconvenient. Room was in a separate annex "
The price is RM844
RM1,048 total
includes taxes & fees
26 Jun - 27 Jun
The Red Lion Inn
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, 271 reviews
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."
The price is RM561
RM626 total
includes taxes & fees
25 Jun - 26 Jun
Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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, 489 reviews
"This was a pleasant place to stay at."
The price is RM702
RM837 total
includes taxes & fees
25 Jun - 26 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Seven Hills Inn
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, 467 reviews
"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
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, 512 reviews
"Everyone is so nice and attentive; the front desk is always professional, specially Maria one of the Manager. I was very happy with the service at the coffee shop. My family and I will always choose this hotel in the Berkshires!! we stay here at least 3 times during the year. "
The price is RM976
RM1,090 total
includes taxes & fees
10 Jul - 11 Jul
Courtyard by Marriott Lenox Berkshires
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, 166 reviews
"The Inn's location has a million dollar lakeview, free breakfasts and free kayaking. This setting is great for mental health. The staff was welcoming, friendly and helpful."
The price is RM707
RM829 total
includes taxes & fees
26 Jun - 27 Jun
Lakehouse Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, 653 reviews
"Great place for a stay. Clean and well run by staff."
The price is RM928
RM1,037 total
includes taxes & fees
26 Jun - 27 Jun
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, 1,003 reviews
"My room was very comfortable. The service was so great! The welcome drink was a lovely treat. Inn was clean and welcoming. I can't wait to go back! "
The price is RM594
RM696 total
includes taxes & fees
27 Jun - 28 Jun
The Cornell Inn, Lenox
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, 609 reviews
"Cozy little room, very clean and comfortable, close to amenities, would definitely stay here again!"
The price is RM403
RM450 total
includes taxes & fees
25 Jun - 26 Jun
Monument Mountain Motel
Apple Tree Inn
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, 223 reviews
"Very nice property. Well maintained and friendly staff. Room was clean and comfortable. We went to a show at Tanglewood and were able to walk from the hotel to the show and back. The only downside to that was walking up the driveway. It was a little steep for being a little out of shape! But the view from this hotel is amazing! So being at the top of a hill is perfect. "
The price is RM938
RM1,048 total
includes taxes & fees
25 Jun - 26 Jun
Apple Tree Inn
Quality Inn
1 bedroom, premium bedding, pillow-top beds, desk
Quality Inn
2.5 star property
8.2 out of 10, Very good, 1,000 reviews
"Property is so convenient to downtown theater and restaurants. Quiet, good parking. Bed a little too soft for me but comfortable otherwise."
The price is RM561
RM626 total
includes taxes & fees
25 Jun - 26 Jun
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Premium bedding, pillow-top 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, 510 reviews
"Very nice place! Great pool and hot tub. A shower at the pool area would’ve been a nice addition to rinse off chlorine. Overall a great value for the money spent. "
The price is RM697
RM779 total
includes taxes & fees
26 Jun - 27 Jun
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, 356 reviews
"Really nice rooms!"
The price is RM1,414
RM1,579 total
includes taxes & fees
25 Jun - 26 Jun
Chambery Inn
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, 35 reviews
"The inn was very quaint and the staff was very friendly. The breakfast was amazing."
The price is RM855
RM984 total
includes taxes & fees
25 Jun - 26 Jun
Blackberry River Inn
Travelodge by Wyndham Great Barrington Berkshires
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, 464 reviews
"Clean basic and friendly! Why overpay elsewhere? Right next to Cafe Adam…. Perfect location"
The price is RM467
RM521 total
includes taxes & fees
25 Jun - 26 Jun
Travelodge by Wyndham Great Barrington Berkshires
The Briarcliff Motel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, 390 reviews
"Liked everything about it"
The price is RM536
RM599 total
includes taxes & fees
25 Jun - 26 Jun
The Briarcliff Motel
The Ponds at Foxhollow by Capital Vacations
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, 110 reviews
"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
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, 386 reviews
"Wonderful place to stay in western Massachusetts."
The price is RM1,064
RM1,168 total
includes taxes & fees
25 Jun - 26 Jun
Shaker Mill Inn
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, 518 reviews
"Found small bugs in the bathroom."
The price is RM405
RM453 total
includes taxes & fees
25 Jun - 26 Jun
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 hotels information

Number of reviews
9,503
Accommodation
681 hotels
Lowest Price
RM403
Highest Price
RM1,414

Destinations near West Stockbridge

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.

Where is the best place 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 traveller 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 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

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

5/5 Excellent
"Clean basic and friendly! Why overpay elsewhere? Right next to Cafe Adam…. Perfect location"
A verified traveller stayed at Travelodge by Wyndham Great Barrington Berkshires
Posted 8 days ago
Travelodge by Wyndham Great Barrington Berkshires
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

5/5 Excellent
"Easy to get to from I90."
A verified traveller stayed at Pleasant Valley Motel West Stockbridge
Posted 1 month ago
Pleasant Valley Motel West Stockbridge