Exclusive Chesterwood Vacation Deals

Chesterwood vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was $757, price is now $646 per person
$646
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,250, price is now $855 per person
$855
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
South Shire

South Shire

4 out of 5
Price was $1,047, price is now $780 per person
$780
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.
Hill Farm Inn

Hill Farm Inn

4 out of 5
Price was $1,219, price is now $955 per person
$955
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This bed & breakfast features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and free perks like full breakfast and free self parking. Enjoy the hot tub and conveniences like limo/town car service and concierge services.
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Manchester Village Historic District
Price was $1,612, price is now $1,375 per person
$1,375
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,521, price is now $1,308 per person
$1,308
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This hotel features an outdoor tennis court and a seasonal outdoor pool. Families will appreciate the picnic area and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.

Frequently asked questions

How much are vacation packages to Chesterwood?
Grab an express ticket to an impressive deal with Travelocity's $646 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 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
$376 nightly
The price is $420 total per night
$420 total
Nov 1 - Nov 2
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

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$191 nightly
The price is $214 total per night
$214 total
Nov 8 - Nov 9
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
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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.