Deals on vacations and trips to Ashuwillticook Rail Trail

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Ashuwillticook Rail Trail flight + hotel vacation packages

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

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $344, price is now $261 per person
$261
per person
Jan 20 - Jan 23
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $547, price is now $401 per person
$401
per person
Jan 20 - Jan 23
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $405, price is now $297 per person
$297
per person
Jan 20 - Jan 23
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $568, price is now $461 per person
$461
per person
Jan 20 - Jan 23
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $318, price is now $264 per person
$264
per person
Jan 20 - Jan 23
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.

Top Ashuwillticook Rail Trail hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$125 nightly
The price is $140 total per night
$140 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $89 total per night
$89 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Dec 22 - Dec 23
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
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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.

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