Stockbridge Vacation Packages 2026 from $857

Stockbridge flight + hotel vacation packages

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

Hotel Brookmere & Arbor Spa

$857

per person

Feb 14 - Feb 20

found 4 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Lodges At Cresthaven

$1,383

per person

Feb 14 - Feb 20

found 4 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Albany (ALB)

A 24-hour gym, free self parking, and laundry facilities are featured at this lodge. WiFi in public areas is free. A business center, a terrace, and a picnic area are also on offer.

27 Lincoln

$1,243

per person

Feb 14 - Feb 20

found 4 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Albany (ALB)

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

The Equinox Golf Resort & Spa

Manchester Village Historic District

$2,344

per person

Feb 14 - Feb 20

found 4 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Albany (ALB)

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Hyatt Place Albany/Downtown

Downtown Albany

$1,095

per person

Feb 14 - Feb 20

found 4 hours ago

Roundtrip non-stop flight included

Greenville (GSP) 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.

Top Stockbridge hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$199 total

Jan 14 - Jan 15, 2026

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

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

Jan 4 - Jan 5, 2026

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, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$85 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$98 nightly

$109 total

Jan 2 - Jan 3, 2026

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Jan 22 - Jan 23, 2026

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$142 total

Jan 20 - Jan 21, 2026

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Pet friendly

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 $857. 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.