Chesterwood Tours

Plan a trip to see Chesterwood

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $602, price is now $407 per person
$407
per person
Jan 21 - Jan 24
found 12 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything was great from the friendly staff to option of restaurants, Every clean and gift shop had a really great time.

Reviewed on Nov 10, 2026

South Shire

South Shire

4 out of 5
Price was $1,410, price is now $1,061 per person
$1,061
per person
Dec 30 - Jan 6
found 20 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
9/10 Wonderful! (137 reviews)

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,234, price is now $941 per person
$941
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (709 reviews)

Stay near popular Chesterwood attractions

Chesterwood

9.2/10 (5 reviews)
You can find out about the history of South Lee with a stop at Chesterwood. Wander the lakeside in this quaint area.
See properties

Best Lodging Options Near Chesterwood

Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
Classic Stockbridge Cottage
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
3-bedroom duplex in Stockbridge on the river

3-bedroom duplex in Stockbridge on the river

Stockbridge MA
3-bedroom duplex in Stockbridge on the river
Tranquil 3 BR Stockbridge House w/ Private Deck!

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge MA
Tranquil 3 BR Stockbridge House w/ Private Deck!
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge MA
Secluded Family Home in Serene Stockbridge Woods
Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness

Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness

Stockbridge MA
Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge MA
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Spacious Retreat Near Tanglewood & Ski Resorts

Spacious Retreat Near Tanglewood & Ski Resorts

Housatonic MA
Spacious Retreat Near Tanglewood & Ski Resorts
See all 772 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