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 3.087.378 ₫ per night from 16 Jul to 17 Jul
3.087.378 ₫
3.448.601 ₫ total
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Noisy upstairs but overall a good experience. Great staff and good breakfast in front office."

Reviewed on 1 Jul 2025

Quality Inn
Prospect Berkshires
Prospect Berkshires
2 out of 5
50 Prospect Lake Rd, Egremont, MA
Get rates
Prospect Berkshires
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 4.335.422 ₫ per night from 13 Jul to 14 Jul
4.335.422 ₫
4.842.667 ₫ total
13 Jul - 14 Jul
includes taxes & fees
8.8/10 Excellent! (632 reviews)
Great place for a stopover, thank you!
"We love staying here in transit to and from Maine and New York every summer. Such a pleasure to know that there are great staff and a great pool! (thank you for always keeping it warm and clean) I'm sure the pool will need to be repainted/resurfaced soon (maybe wait until winter!), but it is always ..."

Reviewed on 26 Jun 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
See all 1,514 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.

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.

Popular places to visit

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

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

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