Ashuwillticook Rail Trail Vacation Packages 2026 from $950

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The Latest Ashuwillticook Rail Trail vacation packages

Price found within the past 48 hours. Click for updated prices.

The Haüs Windham

$950

per person

Oct 17 - Oct 21

just found

Roundtrip flight included

St. George's (BDA) to Hudson (HCC)

7.8/10 Good! (34 reviews)

Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up for all the inconveniences.

Reviewed on Aug 13, 2026

Wylder Hotel Windham

$1,013

per person

Oct 17 - Oct 21

found 2 hours ago

Roundtrip flight included

St. George's (BDA) to Hudson (HCC)

8.8/10 Excellent! (120 reviews)

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

$2,289

per person

Oct 17 - Oct 21

found 2 hours ago

Roundtrip flight included

St. George's (BDA) to Hudson (HCC)

No reviews

Windham NY Escape

$1,108

per person

Oct 17 - Oct 21

just found

Roundtrip flight included

St. George's (BDA) to Hudson (HCC)

10/10 Exceptional! (1 review)

The best

Reviewed on Oct 6, 2025

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Ashuwillticook Rail Trail Hotel Deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

$219 nightly

$254 total

Sep 20 - Sep 21

Total with taxes and fees

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

$151 nightly

$176 total

Sep 7 - Sep 8

Total with taxes and fees

9/10 Wonderful! (2,887 reviews)

"Amazing design and comfortable space. This hotel is very clean and helpful."

Reviewed on Sep 4, 2026

Encore Boston Harbor

1 Broadway Everett MA

Fully refundableReserve now, pay when you stay

$328 nightly

$367 total

Oct 4 - Oct 5

Total with taxes and fees

See all 18,214 properties in Massachusetts

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.