Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $489, price is now $356 per person
$356
per person
Jun 5 - Jun 8
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,202, price is now $866 per person
$866
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.
The Motel Montreal

The Motel Montreal

2 out of 5
Price was $1,111, price is now $845 per person
$845
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
An outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A terrace and a picnic area are also provided.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $501, price is now $385 per person
$385
per person
Jun 5 - Jun 8
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was $1,828, price is now $1,406 per person
$1,406
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A private beach and a hot tub are featured at this smoke-free motel. Enjoy the seasonal outdoor pool and perks like free self parking. A terrace, a picnic area, and laundry facilities are also on offer.
The Lake George Inn

The Lake George Inn

2 out of 5
Price was $1,310, price is now $1,015 per person
$1,015
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with laundry facilities. 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 $356 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 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
$186 nightly
The price is $208 total per night
$208 total
May 17 - May 18
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
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
May 17 - May 18
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
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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.