Ashuwillticook Rail Trail Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Ashuwillticook Rail Trail Vacation Packages

Ashuwillticook Rail Trail Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
8.6/10 Excellent! (1,835 reviews)
"We always stay here because it’s the best value and so beautiful."

Reviewed on Jun 23, 2025

Get rates
Vacation Village in the 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 ₩191,453 per night from Jun 26 to Jun 27
₩191,453
₩233,137 total
Jun 26 - Jun 27
includes taxes & fees
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on Jun 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ₩137,380 per night from Jul 1 to Jul 2
₩137,380
₩153,453 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"I loved everything about this hotel! It was PERFECT! This is my favorite hotel!"

Reviewed on Jun 23, 2025

Best Western Plus Berkshire Hills Inn & Suites
See all 1,074 properties in Ashuwillticook Rail Trail
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.