Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
Price was $183, price is now $149 per person
$149
per person
Feb 19 - Feb 21
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $788, price is now $593 per person
$593
per person
Mar 26 - Mar 30
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $989, price is now $750 per person
$750
per person
Feb 27 - Mar 1
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
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
Save 100% on your flight
Price was $967, price is now $755 per person
$755
per person
Apr 6 - Apr 10
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Luxury Private Estate w Pool Near Rhinebeck

Luxury Private Estate w Pool Near Rhinebeck

2 out of 5
Save 100% on your flight
Price was $2,434, price is now $1,949 per person
$1,949
per person
Apr 6 - Apr 10
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $576, price is now $472 per person
$472
per person
Apr 6 - Apr 10
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's $149 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 1,000,000 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.

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
$335 nightly
The price is $374 total per night
$374 total
Feb 15 - Feb 16
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
This vacation home features a garden, laundry facilities, and barbecue grills.
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
$189 nightly
The price is $212 total per night
$212 total
Jan 26 - Jan 27
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
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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.