A paved path flanked by trees with autumn foliage, a wooden fence, and a clear blue sky.

Ashuwillticook Rail Trail Vacations from $595

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The Latest Ashuwillticook Rail Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
    Dec 11 - Dec 14

    Wylder Hotel Windham + Flight

    Windham
    3 nights
    3.5 star property
    9.0/10 - Wonderful (135 reviews)
    "Room super clean and beautiful property!"
    Reviewed November 2, 2026
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $700
    $595
    per traveler
    found 1 day ago
    Wylder Hotel Windham
  • A lakeside property with a swimming pool, a house, and a well-maintained lawn.
    Dec 19 - Dec 24

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

    Hensonville
    5 nights
    3.0 star property
    Roundtrip • San Juan (SJU) - Hudson (HCC)
    SJU - ALB • 1 stop ALB - SJU • 2 stops
    $6,077
    $4,712
    per traveler
    found 1 day ago
    Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
  • A kitchen with white cabinets, a refrigerator, and a dining area with a table and chairs.
    Dec 11 - Dec 14

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

    Hensonville
    3 nights
    3.0 star property
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $3,204
    $2,555
    per traveler
    found 1 day ago
    Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
  • Front of property
    Dec 11 - Dec 14

    Windham NY Escape + Flight

    Hensonville
    3 nights
    3.0 star property
    10/10 - Exceptional (3 reviews)
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $893
    $815
    per traveler
    found 1 day ago
    Windham NY Escape
  • A wooden cabin with a triangular roof, a wooden door, and a bench outside.
    Dec 11 - Dec 14

    Eastwind Windham + Flight

    Windham
    3 nights
    3.5 star property
    9.2/10 - Wonderful (122 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 October 20, 2026
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $704
    $654
    per traveler
    found 1 day ago
    Eastwind Windham

Ashuwillticook Rail Trail Hotel Deals

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

The Yankee Inn
2.5 star property
11.6 mi from Ashuwillticook Rail Trail
9.2 out of 10, Wonderful, (1,013 reviews)
$116 nightly
The price is $129
Nov 9 - Nov 10
Total with taxes and fees
The Yankee Inn
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.
See all properties in Ashuwillticook Rail Trail
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.