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19 Aug - 20 Aug
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Top Trending Hotels Near Chesterwood

Our top choices for Chesterwood hotels

The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"Loved our visit"
The price is ฿6,159
฿8,336 total
includes taxes & fees
26 Aug - 27 Aug
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is ฿10,062
฿12,172 total
includes taxes & fees
2 Sept - 3 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
7.2 out of 10, Good, (19)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is ฿8,746
฿8,746 total
includes taxes & fees
21 Aug - 22 Aug
Tanglewood Suites
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, (697)
"Pleasant stay"
The price is ฿2,975
฿3,777 total
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (421)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is ฿5,982
฿6,563 total
includes taxes & fees
27 Aug - 28 Aug
Shaker Mill Inn
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, (729)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
The price is ฿5,442
฿6,079 total
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is ฿8,096
฿9,043 total
includes taxes & fees
25 Aug - 26 Aug
Granville House
The Little Lion
Pet-friendly

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (528)
"Comfy, quiet, and clean "
The price is ฿4,844
฿5,411 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
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)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,118
฿4,600 total
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Express Hotel & Suites Great Barrington by IHG
1 bedroom, premium bedding, pillow-top beds, in-room safe

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (649)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is ฿4,032
฿4,503 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (739)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (996)
"Clean and convenient. Great value."
The price is ฿2,260
฿2,480 total
includes taxes & fees
24 Aug - 25 Aug
Pleasant Valley Motel West Stockbridge
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
7.4 out of 10, Good, (544)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,438
฿2,724 total
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ฿4,151
฿5,908 total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is ฿3,565
฿3,982 total
includes taxes & fees
2 Sept - 3 Sept
Quality Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"nice place"
The price is ฿3,012
฿3,365 total
includes taxes & fees
2 Sept - 3 Sept
Quality Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (158)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (29)
"Quit eat and comfortable "
The price is ฿5,006
฿5,592 total
includes taxes & fees
2 Sept - 3 Sept
East Rock 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.

Top Chesterwood Hotel Reviews

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

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

10/10 Excellent
"Pleasant stay"
Lisa 3-night trip
Posted 5 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Very clean, fantastic staff, comfortable bed, robes to use gping to the pool/jacuzzi, plus the large bottles of water in the room. "
Victoria 1-night trip
Posted 5 days ago
The Red Lion Inn

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, take a look at the 8 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 (0.6 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 8 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.