Chesterwood Vacation Deals: Chesterwood, West Stockbridge Holidays

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 Red Lion Inn

30 Main Street, Stockbridge, MA

Free cancellation

Reserve now, pay when you stay

CA $150

per night

Apr. 23 - Apr. 24

Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby. Discover genuine guest reviews for The Red Lion Inn along with the latest prices and availability – book now.

Classic Stockbridge Cottage

Stay at this vacation home in Stockbridge. Enjoy WiFi, onsite parking, and a garden. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby. Discover genuine guest reviews for Classic Stockbridge Cottage along with the latest prices and availability – book now.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183, Stockbridge, MA

Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby. Discover genuine guest reviews for The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood along with the latest prices and availability – book now.

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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.