The Berkshires

Travel Guide

Where to stay in The Berkshires

Private Little Robinhood Lake in the Berkshires , took 2 great pictures here. It was perfectly serene, later in the day and a peaceful quiet you don't often experience in this day and age.

Sherwood Forest

While there might not be top attractions in Sherwood Forest, you can explore the larger area and discover places like Pyramid Lake and Jacob's Pillow.

Sherwood Forest
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is P7,306 per night from 28 Apr to 29 Apr
P7,306
P8,160 total
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (556 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on Apr 14, 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is P6,077 per night from 29 Apr to 30 Apr
P6,077
P7,580 total
includes taxes & fees
Apr 29 - Apr 30
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (620 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on Apr 12, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is P5,498 per night from 30 Apr to 1 May
P5,498
P6,141 total
includes taxes & fees
Apr 30 - May 1
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,002 reviews)
"This place was being remodeled and had I known I would have stayed elsewhere."

Reviewed on Apr 16, 2025

The Yankee, Trademark Collection by Wyndham
See all 1,059 properties 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.
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,796 reviews)
"Wierd very quiet time of year. Properly is outstanding. Hot water in shower took forever. Check in staff seemed like they didnt like each other. Great pool and hot tub. Local restaurants have more color than quality food."

Reviewed on Apr 17, 2025

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (927 reviews)
"Staff was exceptionally helpful and friendly."

Reviewed on Jan 14, 2025

Jiminy Peak Mountain Resort
The Ponds at Foxhollow
The Ponds at Foxhollow
3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on Dec 18, 2024

The Ponds at Foxhollow
See all properties 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.

Popular places to visit

Tanglewood Music Center

Tanglewood Music Center

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Tanglewood Music Center
Hancock which includes signage and fall colors

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Mount Greylock

Mount Greylock

Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.

Mount Greylock
Norman Rockwell Museum

Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum
Bousquet Ski Area

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Bousquet Ski Area

Williams College

Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.

Williams College
Lenox which includes an administrative buidling

Lenox

Photo by Caitlin Reese

Richmond

Photo by Elizabeth Massa Peroulakis

Becket