Stockbridge Vacation Packages 2025/2026 from $517

Stockbridge flight + hotel vacation packages

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

The Wiltwyck

Save 100% on your flight

$517

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Kingston Carriage House

Roundout

Save 100% on your flight

$643

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.

Hutton Brickyards Riverfront Hotel + Venue

Save 100% on your flight

$676

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Save 100% on your flight

$801

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Hotel Kinsley

Kingston Stockade District

$610

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.

Top Stockbridge hotels deals

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free Cancellation

Reserve now, pay when you stay

$227 nightly

$254 total

Aug 26 - Aug 27

Total with taxes and fees

This smoke-free 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. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Spa

Tanglewood Suites

MA-102, Stockbridge, MA

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$269 total

Aug 23 - Aug 24

Total with taxes and fees

A steam room, free self parking, and barbecue grills are featured at this bed & breakfast. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Parking included

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183, Stockbridge, MA

$335 nightly

$374 total

Sep 8 - Sep 9

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

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$145 total

Aug 27 - Aug 28

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

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$96 total

Sep 7 - Sep 8

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

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$104 total

Sep 4 - Sep 5

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.

Popular places to visit

Rockwell called his Stockbridge studio, his “best studio yet.” The building was originally located in the backyard of his home on South Street in Stockbridge, Mass. In 1976, toward the end of his life, Rockwell left the studio and its contents to Norman Rockwell Museum. The building was cut in two and moved to the Museum’s grounds in 1986. #Details

Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

Naumkeag Museum

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

Frequently asked questions

How much are vacation packages to Stockbridge?

Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $517. 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.