Skyline Trail

Popular places to visit

Glendale Falls

Glendale Falls

Commune with nature and explore the great outdoors at Glendale Falls during your travels in Huntington. Wander the lakeside in this relaxing area.

Glendale Falls
Wahconah Falls State Park

Wahconah Falls State Park

Explore the great outdoors at Wahconah Falls State Park and enjoy the mountain views during your trip to Dalton. You can seek out the ski slopes in this quaint area.

Wahconah Falls State Park

Kushi Institute

Enjoy the student vibe at Kushi Institute as part of your travels around Becket. Discover the area's entertainment venues or seek out its hiking trails.

Kushi Institute

Fox Den Wildlife Management Area

You can take time to visit Fox Den Wildlife Management Area during your travels to Worthington. Make some time to visit the shops while you're in the area.

Fox Den Wildlife Management Area

Iroquis Waterfront

Why not spend a lazy afternoon at Iroquis Waterfront during your trip to Becket? Wander the lakeside in this relaxing area.

Iroquis Waterfront

Hiram H. Fox Wildlife Management Area

You can take time to visit Hiram H. Fox Wildlife Management Area during your travels to Huntington. While you're in the area, stroll along the lakeside.

Hiram H. Fox Wildlife Management Area

Top Skyline Trail Hotel Deals

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Berkshires Untold
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Berkshire Mountain Lodge
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Hampton Inn & Suites Berkshires-Lenox
The Constance by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The Constance by the Lenox Collection
Chambery Inn

Chambery Inn

3 out of 5
199 Main St, Lee, MA
Chambery Inn
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Hotel On North
See all 1,727 properties in Skyline 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.