Ashuwillticook Rail Trail Vacation Packages 2026 from $597

The Latest Ashuwillticook Rail Trail vacation packages

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

Hotel Vienna

$597

per person

Dec 17 - Dec 20

found 21 hours ago

Roundtrip non-stop flight included

New York (JFK) to Hudson (HCC)

9.4/10 Exceptional! (878 reviews)

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Save 100% on your flight

$2,840

per person

Dec 9 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Hudson (HCC)

No reviews

Wylder Hotel Windham

$643

per person

Dec 9 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Hudson (HCC)

8.8/10 Excellent! (128 reviews)

Clean and comfortable, but No heater , it was so cold. No free wifi .

Reviewed on Oct 19, 2026

Eastwind Windham

$767

per person

Jan 15 - Jan 18

found 15 hours ago

Roundtrip flight included

Houston (IAH) to Hudson (HCC)

9.2/10 Wonderful! (120 reviews)

Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.

Reviewed on Oct 20, 2026

The Haüs Windham

$1,526

per person

Jan 15 - Jan 18

found 15 hours ago

Roundtrip flight included

Houston (IAH) to Hudson (HCC)

8/10 Very Good! (39 reviews)

Definitely see this place its great

Reviewed on Oct 16, 2026

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Ashuwillticook Rail Trail Hotel Deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

$219 nightly

$255 total

Nov 22 - Nov 23

Total with taxes and fees

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

$105 nightly

$122 total

Nov 22 - Nov 23

Total with taxes and fees

9/10 Wonderful! (2,982 reviews)

"Great staff, gym and coffee shop! Will now stay at the Revolution while my colleagues pay literally 5X to stay at the more well k own hotels."

Reviewed on Oct 22, 2026

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

$176 nightly

$204 total

Nov 22 - Nov 23

Total with taxes and fees

9.6/10 Exceptional! (5,135 reviews)

"This is my second time here! I loved it."

Reviewed on Oct 22, 2026

See all 17,918 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.