Photo by William Keller

Find Hotel with a Concierge in Stockbridge, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotel with a Concierge

This weekend
Next weekend

Top Stockbridge Hotel with a Concierge

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ¥18,605
¥27,710 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Red Lion Inn

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 ¥59,247
¥71,672 total
includes taxes & fees
Dec 18 - Dec 19
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is ¥13,845
¥15,466 total
includes taxes & fees
Dec 11 - Dec 12
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ¥14,148
¥15,803 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ¥40,321
¥50,235 total
includes taxes & fees
Dec 21 - Dec 22
Prospect Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2163)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ¥13,804
¥17,120 total
includes taxes & fees
Dec 7 - Dec 8
Vacation Village in the Berkshires

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ¥17,004
¥18,994 total
includes taxes & fees
Dec 7 - Dec 8
Berkshires Untold

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is ¥20,693
¥23,113 total
includes taxes & fees
Dec 22 - Dec 23
Hotel On North

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is ¥31,026
¥34,656 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Granville House

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ¥28,440
¥31,767 total
includes taxes & fees
Dec 6 - Dec 7
Jiminy Peak Mountain Resort
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