Hotels near Chesterwood

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Top Trending Hotels Near Chesterwood

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

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 P17,990
P21,763 total
includes taxes & fees
Oct 20 - Oct 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1009)
"great place have stayed several times, and hope to return."
The price is P10,405
P14,220 total
includes taxes & fees
Oct 30 - Oct 31
The Red Lion Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (427)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is P10,638
P11,670 total
includes taxes & fees
Oct 1 - Oct 2
Shaker Mill Inn
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, (741)
"The lodging was convenient to all the area attractions."
The price is P7,536
P9,229 total
includes taxes & fees
Oct 2 - Oct 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
The price is P15,637
P17,467 total
includes taxes & fees
Oct 5 - Oct 6
Granville House
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, (738)
"Thank you for nice hospity. Staff was very friendly and professional."
The price is P9,243
P10,324 total
includes taxes & fees
Oct 8 - Oct 9
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Little Lion
Pool

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (534)
"Comfy, quiet, and clean "
The price is P8,080
P9,026 total
includes taxes & fees
Oct 26 - Oct 27
The Little Lion
Monument Mountain Motel
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (759)
"Good value for the price"
Monument Mountain Motel
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (666)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is P7,790
P8,701 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1022)
"Great Indian restaurant in the hotel!"
The price is P6,671
P7,451 total
includes taxes & fees
Oct 27 - Oct 28
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (549)
"Excellent location, friendly service, clean, comfortable room."
The price is P4,360
P4,870 total
includes taxes & fees
Oct 1 - Oct 2
Travelodge by Wyndham Great Barrington Berkshires
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1008)
"Very convenient off I 90 - nice breakfast area - friendly staff"
The price is P5,386
P6,016 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (1007)
"good average place to stay."
The price is P4,041
P4,433 total
includes taxes & fees
Oct 5 - Oct 6
Pleasant Valley Motel West Stockbridge
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1000)
"Nice and clean would stay again."
The price is P5,386
P6,016 total
includes taxes & fees
Oct 14 - Oct 15
Quality Inn
Apple Tree Inn
Seasonal outdoor pool

Apple Tree Inn

3.0 star property
8.6 out of 10, Excellent, (307)
"Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. "
The price is P9,626
P10,753 total
includes taxes & fees
Oct 1 - Oct 2
Apple Tree Inn
East Rock Inn
Private kitchen

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (32)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is P9,522
P10,636 total
includes taxes & fees
Oct 1 - Oct 2
East Rock Inn
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (634)
"This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area."
The price is P3,913
P4,371 total
includes taxes & fees
Oct 27 - Oct 28
Econo Lodge Lee - Great Barrington
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 P7,422
P10,563 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
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
"Beautiful well-maintained property. Very clean every possible convenient you could want. Friendly welcoming staff plan to return to this property often."
Craig 1-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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. 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 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.