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Find Hotels with Free Parking in Stockbridge, MA

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Check availability on Stockbridge Hotels with Free Parking

Our top choices for Stockbridge hotels with parking

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is NT$11,979
NT$14,492 total
includes taxes & fees
Jan 5 - 2026/1/6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Tanglewood Suites

Tanglewood Suites
2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is NT$6,831
NT$6,831 total
includes taxes & fees
Dec 26 - Dec 27
Tanglewood Suites

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is NT$3,129
NT$3,495 total
includes taxes & fees
Jan 15 - 2026/1/16
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is NT$4,046
NT$4,532 total
includes taxes & fees
Dec 22 - Dec 23
Inn at Silver Maple Farm

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is NT$3,356
NT$3,749 total
includes taxes & fees
Dec 18 - Dec 19
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (817)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is NT$3,420
NT$3,821 total
includes taxes & fees
Dec 22 - Dec 23
Berkshires Untold

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1003)
"Clean room, nice location "
United States
Devron
The price is NT$2,360
NT$2,636 total
includes taxes & fees
Dec 29 - Dec 30
Quality Inn Great Barrington

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is NT$5,648
NT$6,624 total
includes taxes & fees
Dec 19 - Dec 20
Lakehouse Inn

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2175)
"Awesome for ski"
United States
Lazar
The price is NT$3,243
NT$3,965 total
includes taxes & fees
Dec 17 - Dec 18
Vacation Village in the Berkshires
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.

Top Stockbridge Hotel Reviews

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