Great Barrington Vacations 2026/2026 from CA $656

Great Barrington flight + hotel packages

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

The Clocktower Hotel at Century House, an Ascend Collection Hotel

CA $656

per person

Jan 27 - Feb 2

found 10 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Cohoes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.

Hilton Garden Inn Albany Airport

CA $730

per person

Jan 27 - Feb 2

found 10 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Hampton Inn & Suites Albany-Downtown

Downtown Albany

CA $1,001

per person

Jan 27 - Feb 2

found 10 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Hyatt Place Albany/Downtown

Downtown Albany

CA $874

per person

Jan 27 - Feb 2

found 10 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

The Century House, an Ascend Collection Hotel

CA $744

per person

Jan 27 - Feb 2

found 10 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.

Top Great Barrington hotels deals

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

Free cancellation

CA $148

CA $165 total

Dec 14 - Dec 15

includes taxes & fees

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Mansfield Park and Housatonic River are located nearby.

Pool

Breakfast included

Quality Inn

372 Main Street Great Barrington MA

CA $105

CA $117 total

Dec 28 - Dec 29

includes taxes & fees

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.

Breakfast included

Parking included

Monument Mountain Motel

247 Stockbridge Rd Great Barrington MA

Free cancellation

Reserve now, pay when you stay

Get rates

Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Housatonic River and Housatonic River Walk are located nearby.

Parking included

Free WiFi

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

CA $360

CA $449 total

Dec 21 - Dec 22

includes taxes & fees

Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA

Free cancellation

Reserve now, pay when you stay

CA $176

CA $196 total

Jan 4 - Jan 5, 2026

includes taxes & fees

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Housatonic River and Housatonic River Walk are located nearby.

Pool

Breakfast included

The Little Lion

506 Stockbridge Road Great Barrington MA

Free cancellation

Reserve now, pay when you stay

CA $152

CA $170 total

Jan 1 - Jan 2, 2026

includes taxes & fees

Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Monument Mountain and Monument Mountain Reservation are located nearby.

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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

Monument Mountain Reservation

You can take time to visit Monument Mountain Reservation during your travels to Great Barrington. While you're here, you can savor the top-notch restaurants.

Ski Butternut

Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.

Mahaiwe Performing Arts Center

You can enjoy a show at Mahaiwe Performing Arts Center on your trip to Great Barrington. While you're here, you can savor the top-notch restaurants.

Great Barrington Vacations

Whether you're going on a weekend break or an extended vacation, it's best to know a couple of things about Great Barrington before setting off.

Great Barrington lies 100 miles (161 kilometers) to the north of New York, a noteworthy city.

With so much to see and do in this corner of The Berkshires, it's easy to understand why 2,000 people choose to call it home.

Places to visit in Great Barrington

Whether you're an expert or total beginner, it's time pull out your skis and enjoy the slopes. Ski Butternut guarantees a world of fun for everybody! Need some more options? Theater can challenge our world views and asks us to aspire to be more. Attend a show at Mahaiwe Performing Arts Center and open your mind to some big ideas. But there's more. A bit of outdoor fun is good for our mental and physical health. Why not take the family and play some sports in the large open space at Lake Mansfield Park?

Where do you fly into for Great Barrington?

Say hello to amazing new experiences in Great Barrington. Once you've stepped out of Bradley International Airport (BDL), the main streets will be just 40 miles (64 kilometers) to the northwest.

Frequently asked questions

How much are vacation packages to Great Barrington?

Your vacation daydreams can become a reality in Great Barrington from an impressive CA $656. Vacation packages include flights and hotels, so they're bound to make booking easy as pie. All you'll have to worry about is getting out there and having a great time.

How long should my Great Barrington vacation be?

There aren't any hard and fast rules when it comes to how long you should spend in Great Barrington, but the majority of people like to stay around 2 nights. Got some flexibility with your departure date? Extend your vacation by an extra night or two. That way, you'll have sufficient time to check out the area's hidden treasures as well.

Where can I get the best vacation package deals for Great Barrington?

Travelocity has everything you need to score a great Great Barrington package deal. Choose from as many as 400 partner airlines and 1,000,000 properties worldwide and put together a vacation package that suits your style. With so much choice, it's easy to organize your next big getaway.

Why should I book my Great Barrington vacation package with Travelocity?

Because life is one amazing journey, and we have everything you need to help you on the way. With our exceptional service and Price Match Guarantee, you can book your trip with confidence. What's more, you can sleep easy on the road knowing you can reach us with our 24/7 support.

Can I save on my Great Barrington car rental if I book it with hotels and flights?

With a Great Barrington vacation package, you can bundle your car, hotel and flight bookings and save a whole lot. If you can't wait to explore the best of this impressive part of the world, why not make a beeline for Times Square? This top sight is 161 kilometers from Great Barrington. With your own wheels, you'll be there before you know it.

Which airport is best for Great Barrington?

Bradley Intl. Airport (BDL) is one of the busiest airports in Great Barrington. It's roughly 64 kilometers southeast of the city center. Your other choices are Albany Intl. Airport (ALB) (72 kilometers away from central Great Barrington) and Stewart Intl. Airport (SWF) (97 kilometers away from central Great Barrington).

What is there to do in Great Barrington?

You'll feel a certain kind of magic as you stroll through the streets of Great Barrington. Housatonic River Walk and Mahaiwe Performing Arts Center are just two attractions that lure visitors to this fantastic city, so add them to your itinerary.

Where should I stay when visiting Great Barrington?

If you're after someplace comfortable to lay your head, check out the Quality Inn. It's the top pick for many travelers.