Skyline Trail Tours and Activities

Plan a trip to see Skyline Trail

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

Kingston Carriage House

4 out of 5
Roundout
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (16 reviews)
one of the best places we’ve stayed at! the poet’s loft is a cozy and quiet two-room suite with two bathrooms. a simple luxury to be enjoyed.

Reviewed on Jun. 12, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
per person
Sep 10 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (34 reviews)
Had an excellent stay at the brand new Brookmere Hotel. The room was clean and comfortable, and the service throughout was top-notch. I want to give a special shoutout to Jose from the restaurant staff, who helped me with a personal request. His kindness and professionalism really stood out. Great hospitality all around — highly recommend!

Reviewed on Jul. 8, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Sep 10 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .

Reviewed on Jun. 1, 2025

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 collegiate vibe at Kushi Institute during your stay in 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

Best Lodging Options Near Skyline Trail

FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
16 Cheshire Road, Pittsfield, MA
FairBridge Inn Express
Quality Inn
Quality Inn
2.5 out of 5
170 Housatonic Street, Lee, MA
Quality Inn
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
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
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Berkshires Untold
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Berkshire Mountain Lodge
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
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Howard Johnson by Wyndham Lenox
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
See all 1,712 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.