Exclusive Chesterwood Vacation Deals

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's Chesterwood vacation package. Not only will you save serious money on your hotel stay and flights, you can also add on some fun local experiences or even a rental vehicle.
Where can I get the best vacation package deals for Chesterwood?
There are fantastic Chesterwood package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 665,000 properties worldwide? Remember this the next time you're ready to check another destination off the old bucket list.
Why should I purchase my Chesterwood vacation package with Travelocity?
We take the stress out of travel planning. Whether you're seeking an amazing new place to explore or want to ensure you get the best price on offer, we're here to assist. Our 24/7 customer support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I go on vacation to Chesterwood at this time?
Don't plan your trip to Chesterwood without the facts about travel restrictions and quarantine policies. Travelocity's Covid-19 Travel Advisor can fill in the blanks. It has all the info you need to make your getaway as relaxed as possible.

Top Chesterwood hotel deals

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 price is CA $430 per night
CA $430
CA $520 total
Feb 15 - Feb 16
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located nearby.
Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
Stay at this vacation home in Stockbridge. Enjoy a garden, laundry facilities, and patios. Popular attractions Chesterwood and Norman Rockwell Museum are located nearby.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $213 per night
CA $213
CA $301 total
Jan 19 - Jan 20
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Don't see what you're looking for?
See all available properties in Chesterwood
View all properties
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.

Best Lodging Options Near Chesterwood