Great Barrington Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Great Barrington

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is 2.437.251 ₫ per night from 17 Sept to 18 Sept
2.437.251 ₫
2.722.410 ₫ total
17 Sept - 18 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."

Reviewed on 22 Aug 2025

Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is 3.268.392 ₫ per night from 1 Sept to 2 Sept
3.268.392 ₫
3.650.795 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (652 reviews)
"Friendly knowledgeable helpful staff"

Reviewed on 24 Aug 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is 3.769.194 ₫ per night from 10 Sept to 11 Sept
3.769.194 ₫
4.210.189 ₫ total
10 Sept - 11 Sept
includes taxes & fees
9.2/10 Wonderful! (732 reviews)
"Had trouble with the remote control for the tv. It claimed to be on one channel but was often on another and couldn't get it to be consistent. Very frustrating."

Reviewed on 24 Aug 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
See all 1,530 properties in Great Barrington
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

Mahaiwe Performing Arts Center

You can make plans for a show at Mahaiwe Performing Arts Center during your trip to Great Barrington. While you're here, you can savour the top-notch restaurants.

Mahaiwe Performing Arts Center

Housatonic River Walk

You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theatre scene and live music.

Housatonic River Walk

Lake Mansfield Park

Explore the great outdoors at Lake Mansfield Park, a lovely green space in Great Barrington. Experience the area's theatre scene and live music.

Lake Mansfield Park

Frequently asked questions

How much does a Great Barrington holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Great Barrington costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Great Barrington?
If you'd like to snag a cheap Great Barrington holiday package, consider visiting in March, April and November. You'll generally find better prices on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Great Barrington?
Generally, a handful of days is enough to tick off the top attractions during your Great Barrington holiday. But if you prefer to have more time to kick back or go on day trips, think about extending your trip.
Is it worth booking a holiday package to Great Barrington?
It's easy to see why a Great Barrington holiday is on the must-do list of many travellers. Well-known attractions like Housatonic River Walk are just the start of what you can explore here.
How to find the best Great Barrington package deals?
Use Expedia's handy filters to find some unbeatable Great Barrington package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Great Barrington package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Great Barrington holiday as a package?
You can enjoy significant savings on your Great Barrington escape by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Great Barrington?
If you've got your Great Barrington travel dates confirmed, book as early as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Great Barrington?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Great Barrington.
  2. Set your budget: Factor in costs such as flights, transportation and food when working out how much to set aside for your trip to Great Barrington. Then, choose a hotel that fits your budget, whether that's a low-cost stay or a lavish getaway.
  3. Decide how long to go for: Now that you know more about Great Barrington, you can figure out the ideal length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Great Barrington holiday package that brings all your bookings together.