Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $521, price is now $430 per person
$430
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a terrace and laundry facilities.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,305, price is now $998 per person
$998
per person
Dec 18 - Dec 21
found 14 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $965, price is now $751 per person
$751
per person
Dec 18 - Dec 21
found 14 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
The Whitlock

The Whitlock

2 out of 5
Price was $512, price is now $432 per person
$432
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,070, price is now $905 per person
$905
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $628, price is now $539 per person
$539
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's $430 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

Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
This vacation home features a garden, laundry facilities, and barbecue grills.
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
$393 nightly
The price is $439 total per night
$439 total
Nov 1 - Nov 2
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.
Pool
Breakfast included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$192 nightly
The price is $215 total per night
$215 total
Nov 11 - Nov 12
Total with taxes and fees
This historic 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. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
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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.