Hotels near Chesterwood
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Tonight
22 Sept - 23 SeptTomorrow
23 Sept - 24 SeptThis weekend
25 Sept - 27 SeptNext weekend
2 Oct - 4 Oct Our top choices for Chesterwood hotels
1. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Linda
S$192
includes taxes & fees
27 Sept - 28 Sept
2. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Wendy
S$156
includes taxes & fees
19 Oct - 20 Oct
3. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
S$206
includes taxes & fees
5 Oct - 6 Oct
4. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
Victor
S$110
includes taxes & fees
1 Oct - 2 Oct
5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Bruce
S$277
includes taxes & fees
27 Sept - 28 Sept
6. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
William
S$167
includes taxes & fees
28 Sept - 29 Sept
7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Susan
S$168
includes taxes & fees
20 Oct - 21 Oct
8. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Kirsty
S$241
includes taxes & fees
18 Oct - 19 Oct
9. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
S$142
includes taxes & fees
1 Oct - 2 Oct
10. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
S$148
includes taxes & fees
18 Oct - 19 Oct
11. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Drue
S$199
includes taxes & fees
28 Sept - 29 Sept
12. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
James
S$283
includes taxes & fees
28 Sept - 29 Sept
13. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
S$232
includes taxes & fees
19 Oct - 20 Oct
14. Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
Sebastien
S$626
includes taxes & fees
29 Sept - 30 Sept
15. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
Kimberly
S$144
includes taxes & fees
18 Oct - 19 Oct
16. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Tracy
S$202
includes taxes & fees
27 Sept - 28 Sept
17. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
Maria Dulce
S$190
includes taxes & fees
19 Oct - 20 Oct
18. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Alexandra
S$366
includes taxes & fees
1 Oct - 2 Oct
19. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Larry
S$177
includes taxes & fees
29 Sept - 30 Sept
20. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Joe
S$151
includes taxes & fees
18 Oct - 19 Oct
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Pleasant Valley Motel West Stockbridge
8/10 Good
"Clean but old and warn. I can't complain, great for the money."
Other attractions near Chesterwood
Norman Rockwell Museum
9.4/10 (347 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
Berkshire Botanical Garden
9.4/10 (14 reviews)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
Mission House
9.6/10 (5 reviews)
You can spend time studying the exhibits at Mission House in Stockbridge. Wander the lakeside in this quaint area.
Naumkeag Museum
9.4/10 (10 reviews)
You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Schantz Galleries
7.2/10 (5 reviews)
You can spend an afternoon studying the exhibits at Schantz Galleries during your travels in Stockbridge. Wander the lakeside in this quaint area.
Art et Industrie
8.0/10 (5 reviews)
You can spend an afternoon exploring the galleries in Art et Industrie during your trip to Great Barrington. Amble around this quaint area's gardens or seek out the hiking trails.
Berkshire Theatre Festival
8.8/10 (3 reviews)
You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.