Ashuwillticook Rail Trail Vacation Packages 2026 from $866

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The Latest Ashuwillticook Rail Trail vacation packages

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

Wylder Hotel Windham

$866

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Grand Rapids (GRR) to Hudson (HCC)

8.8/10 Excellent! (120 reviews)

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

Save 100% on your flight

$3,482

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Save 100% on your flight

$3,680

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

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

Save 100% on your flight

$1,671

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

Eastwind Windham

$991

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Grand Rapids (GRR) to Hudson (HCC)

9.2/10 Wonderful! (116 reviews)

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Ashuwillticook Rail Trail Hotel Deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

$344 nightly

$401 total

Sep 20 - Sep 21

Total with taxes and fees

Seaport Hotel Boston

1 Seaport Lane Boston MA

$299 nightly

$347 total

Sep 20 - Sep 21

Total with taxes and fees

9.6/10 Exceptional! (5,003 reviews)

"It was easy to book in a short time, we needed them in a pinch and it was a nice stay. No mini fridge/microwave amenities and parking was expensive but very clean and quiet and the staff helped answer our questions."

Reviewed on Sep 16, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

$159 nightly

$185 total

Sep 20 - Sep 21

Total with taxes and fees

9/10 Wonderful! (2,918 reviews)

"My husband and I are not used to cramped rooms. The staff was very nice. Lobby very nice. I don't travel light, so it was not the place for us. Neighborhood is amazing. Great location."

Reviewed on Sep 16, 2026

See all 18,083 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.