Hotels near Chesterwood
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Chesterwood hotels
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 Chesterwood0.6 km from Chesterwood
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
Deborah
The price is S$517
includes taxes & fees
7 Jul - 8 Jul
The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,006 reviews)
"Clean room and breakfast"
Raphael
The price is S$262
includes taxes & fees
1 Jul - 2 Jul
Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
Mervin
The price is S$248
includes taxes & fees
1 Jul - 2 Jul
The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (569 reviews)
"Such a peaceful and easy stay!"
Mia
The price is S$127
includes taxes & fees
25 Jun - 26 Jun
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 IHG6.6 km from Chesterwood
9.2 out of 10, Wonderful, (915 reviews)
"Wonderful stay for families."
Kimberly
The price is S$239
includes taxes & fees
30 Jun - 1 Jul
Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
Nicole
The price is S$397
includes taxes & fees
30 Jun - 1 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
9.4 out of 10, Exceptional, (787 reviews)
"Dawn was super helpful in getting us checked in."
Kristen
The price is S$269
includes taxes & fees
30 Jun - 1 Jul
Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (873 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens)
Loved the place."
Yekaterina
The price is S$111
includes taxes & fees
25 Jun - 26 Jun
The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
Stephen
The price is S$548
includes taxes & fees
25 Jun - 26 Jun
East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (49 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
Laura
The price is S$184
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,003 reviews)
"It was a clean, friendly hotel."
Cheri
The price is S$205
includes taxes & fees
7 Jul - 8 Jul
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
Olga V
The price is S$102
includes taxes & fees
29 Jun - 30 Jun
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (587 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
Heather
The price is S$114
includes taxes & fees
25 Jun - 26 Jun
Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (380 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
robert
The price is S$390
includes taxes & fees
8 Jul - 9 Jul
The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (312 reviews)
"A beautiful old inn in the heart of a lovely old town."
Linda
The price is S$224
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
8.8 out of 10, Excellent, (778 reviews)
"very responsive staff excellent check in and check out"
Kathleen
The price is S$215
includes taxes & fees
5 Jul - 6 Jul
The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Mark
The price is S$207
includes taxes & fees
9 Jul - 10 Jul
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place, nice amenities and convenient location, highly recommended."
Arthur
The price is S$315
includes taxes & fees
29 Jun - 30 Jun
Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (990 reviews)
"Great lobby and dining room atmosphere!"
Carin
The price is S$241
includes taxes & fees
29 Jun - 30 Jun
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (669 reviews)
"Decent place.friendly, quiet"
William
The price is S$127
includes taxes & fees
25 Jun - 26 Jun
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.
Compare popular hotels close to Chesterwood
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
 The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 9.2 Wonderful 111 reviews | View | ||||||
 The Red Lion Inn | 8.8 Excellent 1,006 reviews | View | ||||||
 Shaker Mill Inn | 9.6 Exceptional 462 reviews | View | ||||||
 The Little Lion | 8.6 Excellent 569 reviews | View | ||||||
 Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 915 reviews | View |
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
