Name: Berkshires Untold
Price range: $87 total
Rating: 9

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Ashuwillticook Rail Trail vacation packages

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

The Haüs Windham

$581

per person

Apr 17 - Apr 21

found 20 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hudson (HCC)

7.6/10 Good! (25 reviews)

Mainly the location and the solitude.

Reviewed on Feb 7, 2026

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Save 100% on your flight

$4,197

per person

Apr 17 - Apr 21

found 20 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hudson (HCC)

No reviews

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Save 100% on your flight

$4,167

per person

Apr 17 - Apr 21

found 20 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hudson (HCC)

No reviews

Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Save 100% on your flight

$3,885

per person

Apr 17 - Apr 21

found 20 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hudson (HCC)

No reviews

Wylder Hotel Windham

$675

per person

Apr 17 - Apr 21

found 20 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hudson (HCC)

8.6/10 Excellent! (93 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

Don't see what you're looking for?

See all available trips from Columbus to Ashuwillticook Rail Trail

View all trips

Ashuwillticook Rail Trail Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$118 nightly

$132 total

Apr 5 - Apr 6

Total with taxes and fees

8.8/10 Excellent! (1,000 reviews)

For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on Mar 5, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

$121 nightly

$135 total

Mar 19 - Mar 20

Total with taxes and fees

9/10 Wonderful! (878 reviews)

The room is cozy and the kitchen is great. The pool area needs renovation but my kids still love the fact the pool is huge. Only downside is it takes forever to get your $150 deposit refunded:( every time and I leave the room spotless.

Reviewed on Mar 17, 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

$78 nightly

$87 total

Mar 29 - Mar 30

Total with taxes and fees

9/10 Wonderful! (876 reviews)

I always sleep the best here. So quiet and comfortable. Love the lounge area. Bartender really nice. Had a lovely cheese plate. Shower is great. Great value!

Reviewed on Mar 18, 2026

See all 1,116 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.