Ashuwillticook Rail Trail Vacations from $670

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 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

The Latest Ashuwillticook Rail Trail vacation packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Catskills
Coldbrook Bed and Breakfast
Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain
Woodstock Way Hotel
Overlook Hotel
Don't see what you're looking for?
See all available trips from Columbus to Ashuwillticook Rail Trail
View all trips

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
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Aug 10 to Aug 11
$132 total
Aug 10 - Aug 11
Total includes taxes and fees
8.6/10 Excellent! (1,921 reviews)
"Excellent"

Reviewed on Aug 2, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 1 to Sep 2
$120 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (538 reviews)
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."

Reviewed on Aug 3, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $78 total per night from Sep 2 to Sep 3
$78 total
Sep 2 - Sep 3
Total includes taxes and fees
5.2/10 (760 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.