Chesterwood

Plan a trip to see Chesterwood

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La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
No hot water in the sinks, rust in tub area, keys didn’t work properly

Reviewed on Aug 4, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,931 reviews)
The driveways and parking areas are in mediocre condition. The furniture is ok but not as good as in other timeshares we have visited and the kitchenette is functional but as complete as is desirable. However, on the positive side, the property is quiet and surroundings are scenic. It is located in decent proximity to Berkshire attractions (Greylock Glen, Ashuwillticook Rail Trail, Jiminy Peak, The Clark and MASSMoCA, Hancock Shaker Village, Mt. Greylock).

Reviewed on Aug 8, 2025

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8/10 Very Good! (1,009 reviews)
I think the staff does their best to clean, but the rooms are so incredibly old and dingy. The bottom of the bathtub was grey from buildup. Not many towels in the room and an odd odor throughout. The staff however is incredible.

Reviewed on Aug 8, 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 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

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

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
Tranquil 3 BR Stockbridge House w/ Private Deck!

Tranquil 3 BR Stockbridge House w/ Private Deck!

3 out of 5
South Lee
Tranquil 3 BR Stockbridge House w/ Private Deck!
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

Stockbridge
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
See all 750 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.