Book a hotel near Chesterwood, South Lee

Name: The Red Lion Inn
Price range: $214 total

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Top hotels close to Chesterwood

Classic Stockbridge Cottage

Stockbridge MA

0.26 mi from Chesterwood

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This vacation home features a garden, laundry facilities, and barbecue grills.

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

26 Glendale Road, RR 183 Stockbridge MA

0.4 mi from Chesterwood

$358 nightly

$399 total

Sep 28 - Sep 29

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

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Breakfast included

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge MA

0.85 mi from Chesterwood

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This vacation home features laundry facilities.

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Secluded Family Home in Serene Stockbridge Woods

Stockbridge MA

1.11 mi from Chesterwood

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

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Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness

Stockbridge MA

1.45 mi from Chesterwood

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This vacation home features a garden, laundry facilities, and barbecue grills.

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Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

West Stockbridge MA

1.53 mi from Chesterwood

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This apartment features a garden, laundry facilities, and barbecue grills.

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Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway

West Stockbridge MA

1.53 mi from Chesterwood

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This vacation home features a garden, laundry facilities, and barbecue grills.

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Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge MA

1.57 mi from Chesterwood

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This vacation home features a garden, laundry facilities, and barbecue grills.

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8 Mi to Tanglewood & Butternut Ski: Spacious Home!

Housatonic MA

1.59 mi from Chesterwood

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A gym is featured at this vacation home, along with laundry facilities and barbecue grills.

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Hearth House | Prime Location!

Stockbridge MA

1.64 mi from Chesterwood

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A sauna is featured at this vacation home, along with a garden and barbecue grills.

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Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

Stockbridge MA

1.65 mi from Chesterwood

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This vacation home features a garden, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.

Kitchen

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The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

2.06 mi from Chesterwood

$191 nightly

$214 total

Sep 29 - Sep 30

Total with taxes and fees

This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Spa

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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 essential information

Accommodation	770 hotels
Lowest Price	$214
Highest Price	$399
Popular hotels	The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Classic Stockbridge Cottage, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness, Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly., Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway, 8 Mi to Tanglewood & Butternut Ski: Spacious Home!, Forest Views, Enclosed Patio in Secluded Modern Home \| Woodland Zen by AvantStay, Hearth House \| Prime Location!

Recent Chesterwood hotel reviews by fellow wanderers

The Red Lion Inn

5 out of 5

Posted 22 hours ago

Travelocity Verified Review

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

A verified traveler stayed at The Red Lion Inn

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

5 out of 5

Posted 8 days ago

Travelocity Verified Review

"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."

A verified traveler stayed at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

5 out of 5

Posted 2 weeks ago

Travelocity Verified Review

"We love the beautiful Taggart River House! This was our second stay--eight of us really enjoyed our return visit to Stockbridge, Tanglewood and the Berkshires. The location is superb--walking distance to downtown Stockbridge can never be overrated. Short drives to everything else make this property ideal. Super responsive and helpful hosts! Very clean, well-appointed rooms and facilities, more than ample parking and easy-to-follow house rules and recommendations. Pictures are accurate. You will love it!"

A verified traveler stayed at Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Tranquil 3 BR Stockbridge House w/ Private Deck!

5 out of 5

Posted 3 weeks ago

Travelocity Verified Review

"The house is lovely with a quirky charm. It is indeed a tranquil property surrounded by woods. Our hosts have thoughtfully overstocked the premises with towels, sheets, paper goods, and all sorts of kitchen tools and condiments. We had a lovely time."

A verified traveler stayed at Tranquil 3 BR Stockbridge House w/ Private Deck!

Hearth House | Prime Location!

5 out of 5

Posted 2 months ago

Travelocity Verified Review

"This property was better than expected! The photos don’t do it justice. It was ideal for my husband and me to share with our son and small granddaughter with them having their privacy upstairs, but ample room for us to all be together downstairs, and a wonderful bedroom suite for us. The yard and patio are lovely. We so appreciated the ample supplies provided (at some rentals we’ve had to run to a store to augment things that ran out) and the well appointed kitchen. We love the area and we’re only sorry our stay wasn’t long enough to take full advantage of everything on and off site. My only suggestion is that the information provided upon leaving would be helpful to have upfront, particularly because some things mentioned differed from information in the handbook on the property, and it would help to plan better for day of departure. Oh, and communication was terrific with Jayren being very responsive to any questions."

A verified traveler stayed at Hearth House | Prime Location!

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