Deals on vacations and trips to Stockbridge

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Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $616, price is now $519 per person
$519
per person
Jan 19 - Jan 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $909, price is now $673 per person
$673
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This aparthotel 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.
The Whitlock

The Whitlock

2 out of 5
Price was $810, price is now $606 per person
$606
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $707, price is now $557 per person
$557
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This aparthotel 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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
Price was $1,035, price is now $871 per person
$871
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
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.

Top Stockbridge hotels 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
$195 nightly
The price is $218 total per night
$218 total
Nov 12 - Nov 13
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
$356 nightly
The price is $397 total per night
$397 total
Dec 6 - Dec 7
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
Hawthorne House

Hawthorne House

Lenox MA
Get rates
This vacation home features laundry facilities.
Kitchen
Washer
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$281 nightly
The price is $313 total per night
$313 total
Nov 8 - Nov 9
Total with taxes and fees
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. 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 a communal living room are also on offer.
Pool
Breakfast included
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $136 total per night
$136 total
Dec 6 - Dec 7
Total with taxes and fees
This aparthotel 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.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $113 total per night
$113 total
Dec 6 - Dec 7
Total with taxes and fees
This aparthotel 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.
Pool
Hot Tub
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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.

Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
See properties

Frequently asked questions

How much are vacation packages to Stockbridge?
Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $519. Providing both flights and hotels, these terrific deals are a simple way to visit more of our wonderful planet.
How long should my Stockbridge vacation be?
Many visitors stay roughly 2 nights in Stockbridge. But what works for them mightn't work for you. Whether you opt to stay for a few days or a few weeks, you'll enjoy discovering all the wonderful things that this place has to offer.
Where can I get the best vacation package deals for Stockbridge?
There are awesome Stockbridge package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you're ready to cross another place off your travel bucket list.
Why should I book my Stockbridge vacation bundle with Travelocity?
Because we believe in creating unforgettable travel experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our customer support is on hand 24/7 to make sure you're never alone. We also offer a Price Match Guarantee, so you can book your trip knowing you've scored the best deal around. If you find a lower price, we'll match it!
Can I save on my Stockbridge car rental if I book it with my hotel or flight?
Combining your flight, hotel and car into a Stockbridge vacation package is the best way to score better prices. Plus, having your own wheels gives you total freedom to get to all those big sights you'd like to see. Sitting 110 mi away from Stockbridge, Times Square is one attraction that should be on your can't-miss list. Fasten your seat belt and make a day trip of it.
Which airport is best for Stockbridge?
Bradley Intl. Airport (BDL) is popular. It's situated approximately 40 mi southeast of Stockbridge. Other options worth considering are Albany Intl. Airport (ALB) (40 mi away from central Stockbridge) and Hartford, CT (HFD-Hartford - Brainard) (50 mi away from central Stockbridge).
What is there to do in Stockbridge?
There is a certain magic as you wander through the streets of Stockbridge. National Shrine of the Divine Mercy and Norman Rockwell Museum are just a couple of attractions that make this city such a sought-after destination, so put them at the top of your to-do list.
Where should I stay when visiting Stockbridge?
The The Red Lion Inn is recommended by many travelers. Book now before it's too late.

Photos of local treasures

Browse Stockbridge vacation photos for more inspiration

A river surrounded by autumn-colored trees and a forested hill.
A picnic table in a park with autumn leaves on the ground and trees with fall colors in the background.
A lake with a sunset, houses along the shore, and mountains in the background.
A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.
A nighttime view of a residential area with houses adorned with holiday lights.

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