Search Great Barrington Guest Houses

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Great Barrington guest houses

1. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (71 reviews)
"What a unique stay! Wish we could have stayed longer."
United States
Kristina
The price is AU$176
includes taxes & fees
16 Nov - 17 Nov
Hideaway Inn Lenox

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is AU$160
includes taxes & fees
17 Nov - 18 Nov
The Central Downtown Inn & Suites

3. 9 Academy

9 Academy
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (15 reviews)
"Incredible space. I plan on staying again anytime I’m in the area. Wonderful staff, very easy check in and check out. Excellent room and amenities."
United States
Kyle
The price is AU$928
includes taxes & fees
17 Nov - 18 Nov
9 Academy

4. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (302 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is AU$322
includes taxes & fees
24 Nov - 25 Nov
Berkshire Village Carriage House - Super Private!!

5. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (118 reviews)
"This is such a beautiful property it’s worth the trip to Granby alone. Nice waterfall short hike and great ice cream nearby"
United States
Tiffany N.
The price is AU$359
includes taxes & fees
17 Nov - 18 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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.

Learn more about Great Barrington

Tucked in the Berkshires, this charming town blends historic Main Street shopping with easy access to Monument Mountain's panoramic hiking trails. Visit in autumn when the maple-lined streets burst with colour, or catch performances at the Mahaiwe Theatre housed in a beautifully restored 1905 building.

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.