Stockbridge Bowl Tours

Plan a trip to see Stockbridge Bowl

Price found within the past 48 hours. Click for updated prices.
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 $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 1 hour 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

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $5,233, price is now $3,586 per person
$3,586
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (18 reviews)

Popular places to visit

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
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

Frelinghuysen Morris House and Studio

You can spend time exploring the galleries in Frelinghuysen Morris House and Studio during your trip to Stockbridge. Wander the lakeside in this family-friendly area.

Frelinghuysen Morris House and Studio

The Mount

5/5(37 reviews)

You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside.

The Mount

Shakespeare and Company

5/5(28 reviews)

You can get tickets for a performance at Shakespeare and Company during your stay in Lenox. While you're in the area, stroll along the lakeside.

Shakespeare and Company

Lenox Library

4.5/5(3 reviews)

Lenox Library is just one of the places to see in Lenox, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's gardens or attend a sporting event.

Lenox Library

Best Lodging Options Near Stockbridge Bowl

Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!

3 out of 5
Stockbridge MA
Stockbridge Home: Walk to Town Beach!
Summer Cottage at The Lake!

Summer Cottage at The Lake!

Stockbridge MA
Summer Cottage at The Lake!
Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac

Stockbridge MA
Artist's Camp on Lake Mahkeenac
Stockbridge Bowl Lake Community

Stockbridge Bowl Lake Community

Stockbridge MA
Stockbridge Bowl Lake Community
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Apple Tree Inn

Apple Tree Inn

3 out of 5
10 Richmond Mountain Rd Lenox MA
Apple Tree Inn
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge MA
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
The Ponds at Foxhollow
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
The Black Swan Lee - Lenox, an Ascend Collection Hotel
See all 755 properties in Stockbridge Bowl
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.