Chesterwood Tours

Plan a trip to see Chesterwood

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $695, price is now $509 per person
$509
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9/10 Wonderful! (129 reviews)
Rooting for them to make a go of this recently renovated hotel, but the experience was not what one would expect from a 4-star hotel. We had a corner room on a busy street and there was a lot of street noise that could be improved with double-paned windows. The room needed dusting, there was no bath gel in the shower, the walls are thin so could hear our 'neighbors', the kitchen floor needed a sweep, not terrible, but not without crumbs, and worst of all was the refrigerator which was very dirty. There was a slight smell of cooked food as though someone had been eating in there recently.

Reviewed on Sep 3, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $1,081, price is now $809 per person
$809
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,004 reviews)
We love staying here! It’s a must when in Schenectady.

Reviewed on Sep 4, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $1,204, price is now $937 per person
$937
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.4/10 Exceptional! (489 reviews)
Everything was first rate.

Reviewed on Sep 5, 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 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

National Shrine of the Divine Mercy

4.5/5(40 reviews)

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!
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
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
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
Spacious & Modern Berkshires Getaway

Spacious & Modern Berkshires Getaway

Stockbridge
Spacious & Modern Berkshires Getaway
See all 749 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia