Name: The Red Lion Inn
Price range: $259 total
Rating: 8.8

The Red Lion Inn

30 Main Street Stockbridge MA

$231 nightly

$259 total

Jul 23 - Jul 24

Total with taxes and fees

Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...

8.8/10 Excellent! (1,016 reviews)

"This is a historic property with updates needed for the price. It’s an experience above all else with friendly staff and great food options. And walkable around the quaint town with drinks available on the great large front porch."

Reviewed on Jul 15, 2026

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

26 Glendale Road, RR 183 Stockbridge MA

$349 nightly

$389 total

Aug 2 - Aug 3

Total with taxes and fees

Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...

9.2/10 Wonderful! (113 reviews)

"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."

Reviewed on Jul 14, 2026

The Inn at Stockbridge

30 East Street Lee MA

$389 nightly

$435 total

Jul 27 - Jul 28

Total with taxes and fees

Stay at this B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center ...

9.8/10 Exceptional! (99 reviews)

"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."

Reviewed on Nov 24, 2025

See all 1,343 properties in Stockbridge

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.

Historic Stockbridge Villa on 25 acres sleeps 23

Stockbridge MA

Book a stay at this family-friendly vacation home in Lee. Enjoy free WiFi, private pools, and a sauna. Popular attractions National Shrine of the Divine Mercy ...

10/10 Exceptional! (18 reviews)

"Great home, warm and welcoming!! Hosts were great! Very attentive, enjoyed meeting Lisa. Plenty of room for our gathering, accommodations were excellent!"

Reviewed on Jan 25, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,450 reviews)

"Location is beautiful with scenic views. Families love the large pool and sand volleyball court. BBQ grills were in use daily. And the cooler evening lent itself to a lovely firepit. My stay was brief, but this looked like a great place for family reuinions."

Reviewed on Jul 16, 2026

Huttopia Berkshires

312 Kittle Rd Williamstown MA

Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...

9.6/10 Exceptional! (11 reviews)

"We stayed in a Sierra Tiny House for 3 nights in June 2026. The house was very clean, compact but with everything you need, including a fully equipped kitchen. You should be aware that the kid's room has a triple bunk - it might be a challenge if you had an older teen or adult staying in there because ..."

Reviewed on Jun 29, 2026

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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.