Stockbridge Vacation Packages 2026 from $529

Stockbridge flight + hotel vacation packages

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

Vacation Village in the Berkshires

$529

per person

Jul 18 - Jul 20

found 12 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Albany (ALB)

This condo 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.

Hilton Albany

Downtown Albany

$1,292

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

This traditional hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like free train station pick-up.

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

$1,084

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Hyatt Place Albany/Downtown

Downtown Albany

$1,832

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Hampton Inn Albany-Wolf Road (Airport)

$976

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Top Stockbridge hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

$178 nightly

$198 total

Jul 1 - Jul 2

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

26 Glendale Road, RR 183 Stockbridge MA

$358 nightly

$399 total

Jul 1 - Jul 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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$155 nightly

$173 total

Jun 18 - Jun 19

Total with taxes and fees

This lodge 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

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$136 nightly

$152 total

Jun 18 - Jun 19

Total with taxes and fees

This condo 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

461 Pittsfield Rd Lenox MA

$111 nightly

$124 total

Jun 18 - Jun 19

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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

$99 nightly

$111 total

Jun 18 - Jun 19

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.

Breakfast included

Parking 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.

Frequently asked questions

How much are vacation packages to Stockbridge?

Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $529. 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.