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
per person
Sep 7 - Sep 13
found 19 hours ago
Roundtrip flight included
Montreal (YUL) 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 Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Zoom Flume and Durham Center Museum are located nearby.
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
per person
Sep 7 - Sep 13
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
per person
Sep 7 - Sep 13
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
Stay at this 3-star cottage in Stone Ridge. Enjoy free parking, patios, and air conditioning. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Billingswood by Boutiq

Billingswood by Boutiq

2 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
Stay at this vacation home in Athens. Enjoy free parking and a garden. Popular attractions Sleepy Hollow Lake and Max and Lillian Katzman Theater 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 $679 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
Free cancellation
Reserve now, pay when you stay
The price is CA $256 per night
CA $256
CA $348 total
Jul 22 - Jul 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.
Pool
Spa
Classic Stockbridge Cottage

Classic Stockbridge Cottage

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
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 $503 per night
CA $503
CA $609 total
Aug 19 - Aug 20
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.
Pool
Breakfast included
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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