Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $936, price is now $717 per person
$717
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.
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 8 hours 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 8 hours 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.
Lakefront Terrace Resort

Lakefront Terrace Resort

3 out of 5
Price was $1,285, price is now $1,011 per person
$1,011
per person
Jul 16 - Jul 22
found 8 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
The private beach and marina are among the highlights at this hotel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Lake Haven Motel

Lake Haven Motel

2.5 out of 5
Price was $1,413, price is now $1,119 per person
$1,119
per person
Jul 16 - Jul 22
found 8 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A picnic area and luggage storage are also provided.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,107, price is now $898 per person
$898
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's $717 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
$190 nightly
The price is $213 total per night
$213 total
May 6 - May 7
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.