Chesterwood Vacation Deals: Chesterwood, South Lee Holidays

Chesterwood vacation package deals

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

The Manchester View

per person

Jan. 12 - Jan. 16

found 1 day ago

Roundtrip non-stop flight included

Montego Bay (MBJ) to Albany (ALB)

Stay at this hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dana L. Thompson Memorial Park and Lye Brook Falls are located nearby.

The Equinox Golf Resort & Spa

per person

Jan. 12 - Jan. 16

found 1 day ago

Roundtrip non-stop flight included

Montego Bay (MBJ) to Albany (ALB)

Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

South Shire

per person

Jan. 12 - Jan. 16

found 1 day ago

Roundtrip non-stop flight included

Montego Bay (MBJ) to Albany (ALB)

Stay at this 4-star B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.

The Ponds at Foxhollow by Capital Vacations

per person

Dec. 17 - Dec. 20

found 23 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Albany (ALB)

Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.

Club Wyndham Bentley Brook

per person

Dec. 17 - Dec. 20

found 23 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) 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.

Life House Berkshires

per person

Dec. 17 - Dec. 20

found 23 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Albany (ALB)

Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park 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 $779 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 $200

CA $285 total

includes taxes & fees

18 Nov - 19 Nov

Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. 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

Stay at this vacation home in Stockbridge. Enjoy a garden, patios, and cable/satellite TV service. 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

26 Glendale Road, RR 183, Stockbridge, MA

CA $640

CA $774 total

includes taxes & fees

9 Nov - 10 Nov

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.