Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $1,037, price is now CA $788 per person
CA $788
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $1,242, price is now CA $920 per person
CA $920
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was CA $1,722, price is now CA $1,358 per person
CA $1,358
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
Price was CA $1,423, price is now CA $1,201 per person
CA $1,201
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bracewell Park and Massachusetts Museum of Contemporary Art are located nearby.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
Price was CA $1,347, price is now CA $1,137 per person
CA $1,137
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
Price was CA $1,227, price is now CA $1,039 per person
CA $1,039
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lee Library are located nearby.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's CA $788 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

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is CA $202 per night
CA $202
CA $294 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa
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 $454 per night
CA $454
CA $550 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located nearby.
Pool
Breakfast included
Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
Stay at this vacation home in Stockbridge. Enjoy a garden, laundry facilities, and patios. Popular attractions Tanglewood Music Center and Chesterwood are located nearby.
Kitchen
Washer
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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.

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