Skyline Trail

Choose two or more items and save on your trip:

Top Skyline Trail holiday deals

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa
Microtel Inn & Suites by Wyndham Amsterdam
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
Saratoga Casino Hotel
Hilton Garden Inn Albany Airport

Lodging Near Skyline Trail

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Excellent all the way around

Reviewed on 28 Oct 2025

Opens in a new windowBerkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is AU$175 per night from 2 Nov to 3 Nov
AU$175
2 Nov - 3 Nov
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Everything is clean

Reviewed on 27 Oct 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 12 Nov to 13 Nov
AU$115
12 Nov - 13 Nov
includes taxes & fees
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
Heating fine. Room warm

Reviewed on 12 Oct 2025

Opens in a new windowFairBridge Inn Express
Don't see what you're looking for?
See all available properties in Skyline Trail
View all properties
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.