Title: Ashuwillticook Rail Trail Vacation Packages 2026 from $421 | Expedia.com

[Ashuwillticook Rail Trail Travel Guide](https://expedia.com/Ashuwillticook-Rail-Trail.dx811531152953708544)[Hotels in Ashuwillticook Rail Trail](https://expedia.com/Ashuwillticook-Rail-Trail-Hotels.d811531152953708544.Travel-Guide-Hotels)[Vacation Rentals in Ashuwillticook Rail Trail](https://expedia.com/Ashuwillticook-Rail-Trail-Vacation-Rentals.d811531152953708544.Travel-Guide-VacationRentals)[Flights to Ashuwillticook Rail Trail](https://expedia.com/Cheap-Flights-To-Ashuwillticook-Rail-Trail.d811531152953708544.Travel-Guide-Flights)[Car Rentals in Ashuwillticook Rail Trail](https://expedia.com/Car-Rentals-In-Ashuwillticook-Rail-Trail.d811531152953708544.Car-Rental-Guide)

![](https://images.trvl-media.com/place/811531152953708544/1c2ab733-2998-46b6-94e0-15c0716f2da6.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Ashuwillticook Rail Trail Vacations from $421

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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](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wylder Hotel Windham

$421

per person

Apr 10 - Apr 12

found 15 hours ago

Roundtrip flight included

Charleston (CHS) to Hudson (HCC)

8.8/10 Excellent! (80 reviews)

it's sprawling and has a lot of amenities. I think it's fabulous for kids - they had a magic show, cookie decorating, smores. They have an onsite bakery and restaurant. Tubing. They have shuttles, so you don't feel "stuck." It is very family friendly. I would say it's actually for families versus couples.

Reviewed on Feb 22, 2026

![Catskills Retreat w/ Hot Tub, Fire Pit, Pool & Mtn Views The Windham Mountain House by Avantstay](https://images.trvl-media.com/lodging/123000000/122400000/122393500/122393412/355cb32d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Catskills Retreat w/ Hot Tub, Fire Pit, Pool & Mtn Views The Windham Mountain House by Avantstay

Save 100% on your flight

$1,044

per person

Apr 10 - Apr 12

found 15 hours ago

Roundtrip flight included

Charleston (CHS) to Hudson (HCC)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Ashuwillticook Rail Trail

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## 

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## Ashuwillticook Rail Trail Hotel Deals

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$134 nightly

$150 total

Mar 29 - Mar 30

Total with taxes and fees

8.8/10 Excellent! (2,269 reviews)

Great and helpful stuff, clean room.

Reviewed on Feb 27, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true&regionId=811531152953708544)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

$121 nightly

$136 total

Mar 29 - Mar 30

Total with taxes and fees

9/10 Wonderful! (864 reviews)

Overcharged and lied to said security deposit was released back but never was

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=811531152953708544)

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Williams Inn

101 Spring Street Williamstown MA

Fully refundableReserve now, pay when you stay

$187 nightly

$209 total

Mar 3 - Mar 4

Total with taxes and fees

9.6/10 Exceptional! (582 reviews)

nice aesthetics

Reviewed on Feb 24, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true&regionId=811531152953708544)

[See all 1,097 properties in Ashuwillticook Rail Trail](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F28%2F2026&endDate=3%2F1%2F2026&regionId=811531152953708544)

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.

## Find the Best Ashuwillticook Rail Trail Vacation Packages

## Ashuwillticook Rail Trail Essential Information

| Language | English     |
| -------- | ----------- |
| Currency | U.S dollars |

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- [Hertz Rental Cars in Pittsfield ](https://www.expedia.com/Hertz-Car-Rentals-In-Pittsfield.d9478-c40.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Pittsfield ](https://www.expedia.com/Budget-Car-Rentals-In-Pittsfield.d9478-c39.Car-Rental-Guide-Suppliers)
- [National Car Rental Rental Cars in Pittsfield ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Pittsfield.d9478-c42.Car-Rental-Guide-Suppliers)
- [Van Car Rentals in Pittsfield ](https://www.expedia.com/Van-Car-Rentals-In-Pittsfield.d9478-tVan.Car-Rental-Guide-Class)
- [Avis Rental Cars in Pittsfield ](https://www.expedia.com/Avis-Car-Rentals-In-Pittsfield.d9478-c41.Car-Rental-Guide-Suppliers)
- [Alamo Rent A Car Rental Cars in Pittsfield ](https://www.expedia.com/Alamo-Rent-A-Car-Car-Rentals-In-Pittsfield.d9478-c6.Car-Rental-Guide-Suppliers)
- [Thrifty Car Rental Rental Cars in Pittsfield ](https://www.expedia.com/Thrifty-Car-Rental-Car-Rentals-In-Pittsfield.d9478-c45.Car-Rental-Guide-Suppliers)
- [Convertible Car Rentals in Pittsfield ](https://www.expedia.com/Convertible-Car-Rentals-In-Pittsfield.d9478-tConvertible.Car-Rental-Guide-Class)

- [Dalton Vacation Rentals ](https://www.expedia.com/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)
- [Lanesborough Vacation Rentals ](https://www.expedia.com/Lanesborough-Vacation-Rentals.d6005408.Travel-Guide-VacationRentals)
- [Pittsfield Vacation Rentals ](https://www.expedia.com/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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