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Our top choices for Chesterwood hotels

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

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is NT$11,996
NT$14,512 total
includes taxes & fees
Jan 18 - Jan 19
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1003)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NT$4,712
NT$6,666 total
includes taxes & fees
Jan 14 - Jan 15
The Red Lion Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (440)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is NT$3,424
NT$3,756 total
includes taxes & fees
Jan 5 - Jan 6
Shaker Mill Inn
Property amenity
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (814)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NT$3,534
NT$4,561 total
includes taxes & fees
Jan 7 - Jan 8
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is NT$3,455
NT$3,859 total
includes taxes & fees
Jan 5 - Jan 6
The Little Lion
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is NT$7,501
NT$8,797 total
includes taxes & fees
Jan 5 - Jan 6
The Inn at Stockbridge
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (813)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is NT$5,779
NT$6,778 total
includes taxes & fees
Jan 16 - Jan 17
Lakehouse Inn
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NT$1,631
NT$1,789 total
includes taxes & fees
Jan 8 - Jan 9
Pleasant Valley Motel West Stockbridge
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.4 out of 10, Very Good, (1003)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NT$2,579
NT$2,881 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Lee - Lenox South
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8 km from Chesterwood
8.8 out of 10, Excellent, (716)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is NT$3,078
NT$3,438 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (760)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NT$4,240
NT$4,736 total
includes taxes & fees
Jan 19 - Jan 20
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is NT$4,366
NT$4,877 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is NT$12,572
NT$14,043 total
includes taxes & fees
Jan 18 - Jan 19
33 Main
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
6.2 km from Chesterwood
7.6 out of 10, Good, (566)
"Excellent location!!"
United States
Abdul Samad
The price is NT$2,356
NT$2,632 total
includes taxes & fees
Jan 5 - Jan 6
Travelodge by Wyndham Great Barrington Berkshires
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (653)
"The room was clean and the service adequate"
United States
David
The price is NT$2,316
NT$2,587 total
includes taxes & fees
Jan 31 - Feb 1
Econo Lodge Lee - Great Barrington
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock Inn

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is NT$4,055
NT$4,529 total
includes taxes & fees
Feb 1 - Feb 2
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.
View all properties

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
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
Stephanie 2-night trip
Posted 7 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 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

Berkshire Botanical Garden

4.0/5 (1 review)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
See properties

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 10 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. Another good choice is The Red Lion Inn, located 2.1 mi (3.3 km) away.
How many hotels are there close to Chesterwood?
Expedia has 10 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.

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