Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales

Valley Craft Ales

2 out of 5
Price was CA $812, price is now CA $745 per person
CA $745
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this lodge in Wilmington. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions South Main Street and Jim McGrath Gallery and Studio are located nearby.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was CA $1,173, price is now CA $905 per person
CA $905
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $872, price is now CA $752 per person
CA $752
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this 3-star family-friendly condo 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.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,040, price is now CA $936 per person
CA $936
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this 3.5-star hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
Price was CA $1,107, price is now CA $1,012 per person
CA $1,012
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was CA $2,566, price is now CA $2,471 per person
CA $2,471
per person
Oct 30 - Nov 2
found 3 hours ago
Roundtrip flight included
Quito (UIO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall 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 $745 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 $425 per night
CA $425
CA $514 total
Oct 6 - Oct 7
includes taxes & fees
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood 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 $263 per night
CA $263
CA $356 total
Sep 22 - Sep 23
includes taxes & fees
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stay at this vacation home in South Lee. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Berkshire Botanical Garden are located nearby.
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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.

Best Lodging Options Near Chesterwood