Name: Holiday Inn & Suites Pittsfield-Berkshires by IHG
Price range: $109 total
Rating: 8

Photo by Chris Addams

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The Latest Ashuwillticook Rail Trail vacation packages

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

Kaatskill Mountain Club at Hunter Mountain

$943

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Hudson (HCC)

9.2/10 Wonderful! (314 reviews)

Excellent location , great staff and clean room. Very happy with our stay.

Reviewed on Jan 6, 2026

The Haüs Windham

Save 100% on your flight

$1,703

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Hudson (HCC)

8.6/10 Excellent! (17 reviews)

I loved the view and the area

Reviewed on Jul 31, 2025

Hunter Mountain Ski House - Tesla Charger

$3,301

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Hudson (HCC)

No reviews

Wylder Hotel Windham

$948

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Hudson (HCC)

8.8/10 Excellent! (80 reviews)

Very nice hotel. Exactly what we needed.

Reviewed on Jan 2, 2026

Hunter Lodge, a Bluebird by Lark

$1,083

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Hudson (HCC)

9.2/10 Wonderful! (808 reviews)

Great location, very nice common rooms, friendly staff

Reviewed on Jan 8, 2026

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Ashuwillticook Rail Trail Hotel Deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$126 nightly

$141 total

Jan 11 - Jan 12

Total with taxes and fees

8.6/10 Excellent! (2,200 reviews)

Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$125 nightly

$140 total

Feb 2 - Feb 3

Total with taxes and fees

8.6/10 Excellent! (1,001 reviews)

friendly accommodating staff

Reviewed on Jan 1, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Fully refundable

$98 nightly

$109 total

Jan 23 - Jan 24

Total with taxes and fees

8/10 Very Good! (1,007 reviews)

Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN

Reviewed on Jan 4, 2026

See all 1,077 properties in Ashuwillticook Rail Trail

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.