Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
A private beach and an indoor pool are featured at this smoke-free lodge. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
This smoke-free hotel features a golf course, a full-service spa, and 4 restaurants. There's fun for all ages with a playground and an arcade/game room, and complimentary bicycles are available on site. Enjoy the 3 outdoor tennis courts and get free self parking.
English Brook Cottages

English Brook Cottages

3 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this lodge. WiFi in public areas is free. A terrace is also provided.
The Springwater B&B

The Springwater B&B

4 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
This bed & breakfast features a restaurant, a 24-hour gym, and a bar/lounge. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden, a lobby fireplace, and luggage storage are also on offer.
Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
A private beach and a spa 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.
Amsterdam Castle

Amsterdam Castle

3.5 out of 5
per person
Jun 6 - Jun 10
Roundtrip flight included
Grand Junction (GJT) to Albany (ALB)
A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. A terrace and express check-out are also provided.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity’s $1,059 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

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
The price is $106 per night
$106
per night
May 6 - May 7
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and concierge services.
Pet friendly
Breakfast available
Classic Stockbridge Cottage

Classic Stockbridge Cottage

This vacation home includes a garden and barbecue grills.
Pet friendly
Outdoor Space
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
The price is $401 per night
$401
per night
May 5 - May 6
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.
Breakfast included
Pool
Don't see what you're looking for?
See all available properties in Chesterwood
View all properties
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.

Best Lodging Options Near Chesterwood