Chesterwood Tours

Plan a trip to see Chesterwood

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Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $932, price is now $628 per person
$628
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
17.6/10 Exceptional! (2,134 reviews)
Everything is always great here!

Reviewed on Nov 22, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,523, price is now $954 per person
$954
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,320, price is now $829 per person
$829
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Popular places to visit

Rockwell called his Stockbridge studio, his “best studio yet.” The building was originally located in the backyard of his home on South Street in Stockbridge, Mass. In 1976, toward the end of his life, Rockwell left the studio and its contents to Norman Rockwell Museum. The building was cut in two and moved to the Museum’s grounds in 1986. #Details

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.

Norman Rockwell Museum
A relatively easy hike for this nice view.

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.

Monument Mountain Reservation
A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

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.

Tanglewood Music Center

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.

Berkshire Botanical Garden

Mission House

You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.

Mission House

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.

Naumkeag Museum

Best Lodging Options Near Chesterwood

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