Great Barrington Guest Houses | Find the Top Guest Houses in Great Barrington

A large stone church with a tall bell tower and arched windows.

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Our top choices for Great Barrington guest houses

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

1. Hideaway Inn Lenox

Lenox

Barbara

includes taxes & fees

5 Oct - 6 Oct

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

Pittsfield

Rena

includes taxes & fees

7 Oct - 8 Oct

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

3. Berkshire Village Carriage House - Super Private!!

Lanesborough

Mary R.

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a dining area, a large window, and a view of the garden.

4. 9 Academy

Salisbury

Kyle

includes taxes & fees

4 Oct - 5 Oct

A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

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

Granby

Kristen S.

includes taxes & fees

13 Oct - 14 Oct

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Top Great Barrington Hotel Reviews

The Yankee Inn

8/10 Good

"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"

The Red Lion Inn

10/10 Excellent

"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."