Downtown Great Barrington Holidays from £1,256
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Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
£1,472
per person
29 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Dublin (DUB) to Albany (ALB)
6/10 (1 review)
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life.
The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.
Reviewed on 23 Aug 2025
Top hotels in Downtown Great Barrington
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
£63
22 Nov - 23 Nov
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"
Reviewed on 26 Oct 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£88
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,232 reviews)
"Tried to rate 5 but font on iPhone wouldn’t let me. Loved everything but sad hot tub was down and not mentioned on website"
Reviewed on 26 Oct 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£86
10 Nov - 11 Nov
includes taxes & fees
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.
Stay near popular Downtown Great Barrington attractions
Mahaiwe Performing Arts Center
9.0/10 (22 reviews)
Enjoy a stop at Mahaiwe Performing Arts Center, an entertaining place to visit in Great Barrington. While you're here, you can savour the top-notch restaurants.
Housatonic River Walk
9.2/10 (76 reviews)
You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theatre scene and live music.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.