Chesterwood Tours
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Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa
Save 100% on your flight
Price was $372, price is now $236 per person
$236
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!
Reviewed on Dec 1, 2025
The Landing Hotel at Rivers Casino & Resort
Stockade Historic District
Price was $757, price is now $500 per person
$500
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!
Reviewed on Nov 23, 2025
Pocketbook Hotel and Bath
Save 100% on your flight
Price was $716, price is now $474 per person
$474
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us
Reviewed on Dec 9, 2025
Popular places to visit
Norman Rockwell Museum
4.5/5(193 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
Monument Mountain Reservation
You can take time to visit Monument Mountain Reservation during your travels to Great Barrington. While you're here, you can savor the top-notch restaurants.
Tanglewood Music Center
5/5(150 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
Berkshire Botanical Garden
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
You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.
Naumkeag Museum
You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.
Best Lodging Options Near Chesterwood
Check availability on hotels close to Chesterwood
The Red Lion Inn
30 Main Street Stockbridge MA
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
Classic Stockbridge Cottage
Stockbridge MA
Completely Renovated Historic Home in the Heart of the Berkshires
Glendale MA
Tranquil 3 BR Stockbridge House w/ Private Deck!
South Lee MA
Lofted Hideaway on Pixley Hill
West Stockbridge MA
Secluded Family Home in Serene Stockbridge Woods
Stockbridge MA
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
Stockbridge MA
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge MA
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.
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- Schantz Galleries
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