Chesterwood Tours

Plan a trip to see Chesterwood

Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $663, price is now $559 per person
$559
per person
Dec 16 - Dec 20
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (709 reviews)

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Save 100% on your flight
Price was $1,580, price is now $1,220 per person
$1,220
per person
Dec 27 - Jan 2
found 3 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9/10 Wonderful! (405 reviews)

Luxury Private Estate w Pool Near Rhinebeck

Luxury Private Estate w Pool Near Rhinebeck

2 out of 5
Save 100% on your flight
Price was $11,705, price is now $9,710 per person
$9,710
per person
Dec 27 - Jan 2
found 3 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
No 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