Great Barrington Vacation Homes

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

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Our top choices for Great Barrington holiday homes

Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Great Barrington

Julie J.

HK$3,075 total

includes taxes & fees

19 Jul - 20 Jul

Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

HK$2,594 total

includes taxes & fees

29 Jul - 30 Jul

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

HK$10,396 total

includes taxes & fees

23 Jul - 24 Jul

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington

James M.

HK$19,934 total

includes taxes & fees

2 Aug - 3 Aug

All the comforts of home

Hudson

Julie B.

HK$1,108 total

includes taxes & fees

23 Jul - 24 Jul

Big farmhouse in the foothills of the Berkshires

Russell

Will G.

HK$2,784 total

includes taxes & fees

26 Jul - 27 Jul

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

HK$1,581 total

includes taxes & fees

26 Jul - 27 Jul

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

HK$3,669 total

includes taxes & fees

19 Jul - 20 Jul

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Top Great Barrington Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Great location and very convenient setup if you like privacy and cooking"

The Yankee Inn

10/10 Excellent

"All in all a great stay ! We stay at the Yankee Inn during our summer jaunts to the area. The staff is most kind, and helps greatly in our accommodation requests. Clean room, easy access, breakfast area and food is just what you need to start the day. A nice lobby has all area guides available as well as small items to purchase for snack. Great Pool indoors and outside too. kudos."

Pocketbook Hotel and Bath

10/10 Excellent

"I'm house-hunting in Hudson, so my wife and I have stayed in a few other hotels and B&Bs there. However, one night in Pocketbook and I'll definitely continue booking there. I don't understand the complaints about the noise or rude staff, becauee we experienced the exact opposite. The staff were warm & welcoming, and very friendly. Overnight, it was peaceful and quiet. We stayed on a Saturday night and the hotel was booked out, but besides hearing some light noise above us the next day, it was peaceful. We stayed in the 250 sqft studio, and although on the smaller side, it was super efficient with a smart layout. Huge mirror on the wall near the exit, a mini bar, toiletries, excellent fade lighting and ample electrical outlets. No TV, but a HUGE projector available to watch streaming channels without needing to log in. The only caveat is when you lower the projector screen, you're also covering up the outside light from getting in. It was a Saturday night, and during check-in we were told about Clutch, a cool 'dance club'space in the lower level. The DJ was phenomenal! Checkout was a breeze and Alice was super friendly and accommodating. I LOVE Pocketbook and will definitely return again and again!"

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