Chesterwood Tours

Plan a trip to see Chesterwood

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The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $555, price is now $388 per person
$388
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (1,014 reviews)
Very nice staff great room a lot to do around

Reviewed on Oct 5, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $1,133, price is now $795 per person
$795
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Needs hand rails in shower

Reviewed on Oct 6, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $1,279, price is now $947 per person
$947
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (2,006 reviews)
There were a couple of issues withy stay 10/4/26 to 10/5/26. The staff did not answer my text messages sent as they said they were very busy. The room has small insects and flies. It was reported and staff offered to send maintenance to check on the unit. I was moved to another unit 10/5/25 through 10/6/25. I stay at VV every 2 to months and This has only happened one other time.

Reviewed on Oct 7, 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

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

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

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
26 Glendale Road, RR 183, Stockbridge, MA
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The Red Lion Inn
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge
Secluded Family Home in Serene Stockbridge Woods
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
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
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
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,...
Spacious & Modern Berkshires Getaway

Spacious & Modern Berkshires Getaway

Stockbridge
Spacious & Modern Berkshires Getaway
See all 752 properties in Chesterwood
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.

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