Chesterwood
Visit Chesterwood
Popular places to visit

Norman Rockwell Museum
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to 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 savour the top-notch restaurants.

Tanglewood Music Center
You can make plans for a show at Tanglewood Music Center during your stay in 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 studying the exhibits at Mission House in Stockbridge. Wander the lakeside in this quaint area.
Naumkeag Museum
You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.
Top Hotel Deals

The Red Lion Inn

Tanglewood Suites

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

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views,...

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

Stockbridge Retreat w/ Pool & Hot Tub!

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Explore a world of travel with Expedia
- Holidays and getaways similar to Chesterwood
- Hotels Near Chesterwood, South Lee
- Hotels near other Attractions
- Expedia's Latest Trends
- Stockbridge Retreat w/ Pool & Hot Tub!
- Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
- Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
- Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Stockbridge Village in Summer
Expedia's Latest Trends
- Apartamentos Teneguia
- Hotel Domomea
- 5 Star Hotels in Clonbur
- Holiday Inn Naples by IHG
- 5 Star Hotels in Sorrento Coast
- Hotels near Salem Witch Museum
- The Mad Hatter Hotel
- Hotels in Carcassonne
- B&B Connemara
- Killaloe Hotel & Spa
- Hotels in Dunshaughlin
- Maritina Hotel
- Hotels near The Lynn Auditorium
- TravelodgeIreland Hotels in Shannon
- Hotels with Breakfast in Waterford
- B&B Multyfarnham
- Hotels near Ross Castle