Deals on vacations and trips to Stockbridge

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Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $836, price is now $702 per person
$702
per person
Oct 16 - Oct 20
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.
South Shire

South Shire

4 out of 5
Price was $1,227, price is now $972 per person
$972
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,198, price is now $997 per person
$997
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $849, price is now $726 per person
$726
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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 White House Inn

The White House Inn

3.5 out of 5
Price was $1,318, price is now $1,129 per person
$1,129
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

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
$226 nightly
The price is $252 total per night
$252 total
Sep 7 - Sep 8
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
$358 nightly
The price is $399 total per night
$399 total
Aug 24 - Aug 25
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 Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$415 nightly
The price is $463 total per night
$463 total
Sep 7 - Sep 8
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
Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres

Stockbridge MA
Get rates
This vacation home features an outdoor pool and a sauna. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.
Pool
Kitchen
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
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $178 total per night
$178 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
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.
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Frequently asked questions

How much are vacation packages to Stockbridge?
Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $702. 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 nighttime view of a residential area with houses adorned with holiday lights.
A calm lake reflecting a forest with autumn foliage.
A lake surrounded by autumn-colored trees and hills under a cloudy sky.
A white colonial-style house with black shutters, surrounded by a white picket fence and lush greenery.
A large stone house with green shutters and a steep roof, surrounded by lush trees and a well-maintained lawn.

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