Exclusive Chesterwood Vacation Deals
Chesterwood vacation package deals
Price found within the past 48 hours. Click for updated prices.
The Dewey
Price was $550, price is now $442 per person
$442
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Prospect Berkshires
Price was $730, price is now $523 per person
$523
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Landing Hotel at Rivers Casino & Resort
Nothside
Price was $809, price is now $617 per person
$617
per person
Mar 6 - Mar 10
found 2 hours ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Gedney Farm
Price was $606, price is now $466 per person
$466
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.
The Cornell Inn, Lenox & The Berkshires
Price was $647, price is now $503 per person
$503
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Wilder House Berkshires
Price was $590, price is now $479 per person
$479
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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
Top Chesterwood hotel deals
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night
$462 total
Jan 25 - Jan 26
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
Stockbridge MA
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$182 nightly
The price is $204 total per night
$204 total
Jan 20 - Jan 21
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.
Pool
Spa
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.