
Ashuwillticook Rail Trail Vacations from $321
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The Latest Ashuwillticook Rail Trail vacation packages
Price found within the past 48 hours. Click for updated prices.



Woodstock Way Hotel
Save 100% on your flight
Price was $1,275, price is now $972 per person
$972
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Hudson (HCC)
9.4/10 Exceptional! (164 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.
Reviewed on Aug 18, 2025


Coldbrook Bed and Breakfast
Save 100% on your flight
Price was $512, price is now $392 per person
$392
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Hudson (HCC)
10/10 Exceptional! (7 reviews)
Superbly designed B&B where comfort is found in every detail - from the beds to the fire pit with s'mores kits to the breakfast choices. Amazing experience - the modern, fresh and inviting design of this B&B is nestled in the woods with views of the mountains. We spent a long weekend here, exploring the local towns and trails by day, happy to come home to this lovely B&B every evening. We'll be back!
Reviewed on Aug 4, 2025
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Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total includes taxes and fees
8.6/10 Excellent! (1,950 reviews)
Love Vacation Village!
"Love everything about this place. If you want a true home away from home this is the place. The only miss is streaming abilities for at night, but an extra hdmi to type C cable,and we were all set!"
Reviewed on Aug 16, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (571 reviews)
"Shower/tub side in accessible room was extremely high fyi."
Reviewed on Aug 17, 2025

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Aug 24 to Aug 25
$170 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Walking distance to MassMOCA and several good restaurants and coffee shops."
Reviewed on Aug 15, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.