Exclusive Chesterwood Vacation Deals
Chesterwood vacation package deals
Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge
Price was $496, price is now $375 per person
$375
per person
Dec 19 - Dec 22
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
The Equinox Golf Resort & Spa
Price was $934, price is now $669 per person
$669
per person
Nov 28 - Dec 2
found 10 hours ago
Roundtrip flight included
Tampa (TPA) 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.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Price was $739, price is now $603 per person
$603
per person
Dec 19 - Dec 22
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
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.
Aspen At Manchester
Price was $701, price is now $586 per person
$586
per person
Nov 28 - Dec 2
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.
Seesaw's Lodge
Price was $1,089, price is now $926 per person
$926
per person
Nov 28 - Dec 2
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
A restaurant and a bar/lounge are featured at this lodge. Families will appreciate the arcade/game room, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
Hotel Downstreet, an Ascend Collection Hotel
Price was $620, price is now $533 per person
$533
per person
Dec 19 - Dec 22
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and perks like free self parking.
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
$335 nightly
The price is $374 total per night
$374 total
Oct 14 - Oct 15
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
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
$217 nightly
The price is $243 total per night
$243 total
Sep 29 - Sep 30
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.