Chesterwood Tours and Activities



Popular places to visit


Top Chesterwood Hotel & Accommodation Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
Tanglewood Suites
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

Stockbridge
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

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

3 out of 5
Glendale
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

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

2 out of 5
Stockbridge
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views,...

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

West Stockbridge
Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views,...
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay

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

Stockbridge
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge Retreat w/ Pool & Hot Tub!

3 out of 5
Glendale
Stockbridge Retreat w/ Pool & Hot Tub!
Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge

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

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