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 Chesterwood Hotel Deals
Check availability on hotels close to Chesterwood
The Red Lion Inn
Tranquil 3 BR Stockbridge House w/ Private Deck!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Little Lion
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
The Inn at Stockbridge
Great Barrington Lakeside Getaway w/ Kayak & Grill
Explore a world of travel with Expedia
- Adams Hotels
- Agawam Hotels
- Amherst Hotels
- Becket Hotels
- Gay friendly Hotels in Cheshire
- Cheshire Hotels
- Chester Hotels
- Chesterfield Hotels
- Budget Hotels in Chicopee
- Cummington Hotels
- Dalton Hotels
- Resorts in Dalton
- Hotels near Deerfield Academy
- Deerfield Hotels
- Condo Rentals in Drury
- Drury Hotels
- Florida Hotels
- Goshen Hotels
- Great Barrington Hotels
- Hadley Hotels
- Hancock Hotels
- Hatfield Hotels
- Holyoke Hotels
- Huntington Hotels
- Lanesborough Hotels
- Lee Hotels
- Lenox Hotels
- Longmeadow Hotels
- Hotels near MGM Springfield
- Monterey Hotels
- Hotels near Mount Greylock State Reservation Visitor Center
- Cottages in New Ashford
- Hotels with Hot Tubs in North Adams
- North Adams Hotels
- Hotels with Swimming Pools in Northampton
- Hotels with smoking rooms in Northampton
- Luxury Hotels in Northampton
- Otis Hotels
- Savoy Hotels
- Sheffield Hotels
- Hotels with Air Conditioning in South Egremont
- Hotels with Restaurants in South Egremont
- Pet friendly Hotels in South Egremont
- South Egremont Hotels
- South Hadley Hotels
- Southampton Hotels
- Southwick Hotels
- Budget Hotels in Springfield
- Springfield Hotels
- Hotels with Swimming Pools in Stockbridge
- Stockbridge Hotels
- B&B in Sunderland
- Hotels near Tanglewood Music Center
- Apartments in The Berkshires
- Hotels with Waterparks in The Berkshires
- Pet friendly Hotels in The Berkshires
- Motels in The Berkshires
- Resorts in The Berkshires
- Hotels with kitchenette in West Springfield
- West Springfield Hotels
- Business Hotels in West Stockbridge
- Apartments in Western Massachusetts
- Condo Rentals in Western Massachusetts
- Hotels with Hot Tubs in Western Massachusetts
- Hotels with kitchenette in Western Massachusetts
- Hotels with Swimming Pools in Western Massachusetts
- Westfield Hotels
- Williamstown Hotels
- Windsor Hotels
- Flights to Amherst
- Flights to Cheshire
- Flights to Conway
- Flights to Great Barrington
- Flights to Lee
- Flights to North Adams
- Flights from Westover Metropolitan
- Flights from Cheshire
- Flights from Northampton
- Flights from Bangkok (BKK) to Springfield (CEF)
- Flights from Los Angeles (LAX) to Westfield (BAF)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.