Great Barrington Vacations from $492

For families looking to book the best vacation packages in Great Barrington, consider a stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. This hotel, rated 8.7 out of 10, offers family rooms, a game room, and an indoor pool, with travelers frequently highlighting its spacious rooms and accommodating staff.


Couples seeking a romantic Great Barrington vacation package might enjoy The Old Inn On The Green. This 4-star property, rated 9.4 out of 10, features a bar/lounge, an outdoor pool, and a restaurant, and travelers praise its attentive staff, clean rooms, and delicious food.


If you're looking for a great value, a Great Barrington vacation package with a stay at Quality Inn Great Barrington is a strong choice. Rated 8.4 out of 10, it includes free breakfast and free WiFi, and travelers often mention the wonderful staff and that they would definitely stay here again.

When you bundle, you can save up to 30%*. To save money on a Great Barrington package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Great Barrington is a strong choice for family vacation packages, especially for those seeking outdoor activities and a comfortable stay in a ski destination.


Families can enjoy winter sports at Ski Butternut, located about 5 miles from central Great Barrington, or spend time outdoors at Lake Mansfield Park, which is about a 10-minute walk from the center. These attractions provide diverse options for family fun.


For accommodation, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, rated 8.7 out of 10 by travelers, is a great family hotel option. It features family rooms, a game room, an indoor pool, and free breakfast, with guests often praising its spacious rooms and accommodating staff. This makes planning a family vacation package in Great Barrington both convenient and enjoyable.

Great Barrington ski vacation packages typically bundle flights with lodging near the area's ski resorts. For example, a Great Barrington vacation package could include a stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, rated 8.7 out of 10 and about 2 miles from Ski Butternut, offering an indoor pool; travelers often highlight its spacious rooms and great location. Another option is the 4-star The Old Inn On The Green, rated 9.4 out of 10 and about 6 miles from Ski Butternut, which features an outdoor pool and restaurant, with guests frequently praising the attentive staff and delicious breakfast. Lift tickets, equipment rentals, and lessons are generally separate unless specifically noted in your package details.

Many Great Barrington vacation packages include hotels with mountain-view rooms, with about half of package hotels offering this option. When building your Great Barrington vacation package, consider properties like Prospect Berkshires, rated 9.6 out of 10 by travelers, or Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, rated 8.7 out of 10. Keep in mind that specific mountain views depend on the room type and rate booked.

A Great Barrington vacation offers a blend of outdoor adventure and cultural experiences in this ski destination outside a city:


Browse and book things to do in Great Barrington on Expedia.

For a Great Barrington vacation package, a rental car offers the most flexibility, especially for exploring beyond the immediate downtown area. While the downtown area is easily walkable for local shops and restaurants, reaching many of the region's attractions requires transportation.


To visit ski resorts like Ski Butternut, about 5 miles away, or Catamount Ski Area, about 13 miles away, a car or bicycle is necessary. If you're arriving by air, Hartford's Bradley International Airport (BDL) is about 43 miles from central Great Barrington, making a rental car a practical choice for direct travel to your accommodation and for exploring the wider Berkshire region during your Great Barrington vacation packages with flights.

Great Barrington vacation package hotels offer a range of locations, from central spots to those a bit further out, providing access to both town amenities and ski areas.


East Rock Inn is conveniently located about 1 mile from central Great Barrington, placing you close to both downtown and about 1 mile from Ski Butternut. Similarly, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires sits about 1 mile from the center, offering easy access to town and about 2 miles from Ski Butternut.


For a slightly more secluded stay, Prospect Berkshires is about 4 miles from central Great Barrington and about 7 miles from Ski Butternut. This range allows travelers to choose between being closer to town amenities or having a bit more space while still being within a short drive of the main attractions.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Great Barrington vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Great Barrington, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Great Barrington vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Great Barrington getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.