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Our top choices for Great Barrington vacation homes
1. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is AED 817
AED 1,277 total
includes taxes & fees
13 Oct - 14 Oct
2. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (28 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host … and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Kelly B.
The price is AED 716
AED 1,128 total
includes taxes & fees
26 Oct - 27 Oct
3. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
Mark M.
The price is AED 1,469
AED 2,552 total
includes taxes & fees
19 Oct - 20 Oct
4. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (9 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
Roberta
The price is AED 2,089
AED 4,890 total
includes taxes & fees
12 Oct - 13 Oct
5. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
Peter S.
The price is AED 735
AED 1,288 total
includes taxes & fees
13 Oct - 14 Oct
6. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is AED 651
AED 1,569 total
includes taxes & fees
3 Nov - 4 Nov
7. Treetop Hideaway in Tyringham
Treetop Hideaway in TyringhamMonterey
9.0 out of 10, Wonderful, (12 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
Samantha G.
The price is AED 995
AED 2,073 total
includes taxes & fees
9 Nov - 10 Nov
8. Spacious Central Berkshires Home for Groups
Spacious Central Berkshires Home for GroupsLee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
Beth S.
The price is AED 1,074
AED 2,168 total
includes taxes & fees
12 Oct - 13 Oct
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.
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Top Great Barrington Hotel Reviews
Cozy 1-bedroom studio in serene Great Barrington with AC
10/10 Excellent
