Chesterwood Tours and Activities
Visit Chesterwood
Plan a trip to see Chesterwood
Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales
Price was CA $1,466, price is now CA $1,222 per person
CA $1,222
per person
Oct 17 - Oct 24
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Albany (ALB)
8.6/10 Excellent! (143 reviews)
This is a unique stay. I really enjoyed it and would go back. Pictures are accurate. Bare bones, but great price. LOVED the town and area. Comfy bed. Small, but super clean hot water shower. Live music on the weekend - enjoy it!! - done fairly early. No big deal.
Reviewed on Aug. 10, 2025
The Equinox Golf Resort & Spa
Price was CA $2,591, price is now CA $1,879 per person
CA $1,879
per person
Oct 17 - Oct 24
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Albany (ALB)
7.4/10 Good! (512 reviews)
Historical Landmark. The building is full of history. The service and amenities are wonderful especially considering the history of the building. Beautiful place to stay, relax, and unwind. Mountain views are spectacular. Restaurants are wonderful. Everything is convenient. Staff are friendly and welcoming. I am very happy and would recommend this place to anyone.
Reviewed on Aug. 27, 2025
Kimpton Taconic Hotel by IHG
Price was CA $3,061, price is now CA $2,701 per person
CA $2,701
per person
Oct 17 - Oct 24
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Albany (ALB)
9.4/10 Exceptional! (791 reviews)
The staff was really friendly and helpful.
The coffee provided was unfortunately only lukewarm, and the popcorn supply seemed a little short. But, on the other hand no other hotel has ever provided free popcorn for us
Reviewed on Aug. 27, 2025
Popular places to visit
Norman Rockwell Museum
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
Tanglewood Music Center
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.
National Shrine of the Divine Mercy
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.
Best Lodging Options Near Chesterwood
Check availability on hotels close to Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
The Red Lion Inn
30 Main Street, Stockbridge, MA
Tranquil 3 BR Stockbridge House w/ Private Deck!
South Lee
Secluded Family Home in Serene Stockbridge Woods
Stockbridge
Tanglewood Suites
MA-102, Stockbridge, MA
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
Stockbridge
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Glendale
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Stockbridge
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge
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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Vacations and getaways similar to Chesterwood
- Other Hotels near Chesterwood, South Lee
- Hotels near popular South Lee Attractions
- More Hotel Options in Chesterwood
- Spacious & Modern Berkshires Getaway
- Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
- Stockbridge Retreat w/ Pool & Hot Tub!
- Secluded Mountaintop Retreat in the Heart of the Berkshires
- A Grand property in Historic Stockbridge
- Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
- Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
- Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
- Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Stockbridge Village in Summer
- Pleasant Valley Motel West Stockbridge
- Hotels near Tanglewood Music Center
- Hotels near National Shrine of the Divine Mercy
- Hotels near Catamount Ski Area
- Hotels near Norman Rockwell Museum
- Hotels near Ski Butternut
- Hotels near Lee Premium Outlets
- Hotels near Jacob's Pillow
- Hotels near The Mount
- Hotels near Bousquet Ski Area
- Hotels near Taconic State Park
- Hotels near Catamount Aerial Adventure Park
- Hotels near Naumkeag Museum
- Hotels near Hancock Shaker Village
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Berkshire Botanical Garden
- Hotels near Berkshire Museum
- Hotels near Housatonic River
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Housatonic River Walk
- Hotels near Shakespeare and Company