Skyline Trail Tours

However many steps it takes you to finish Skyline Trail, it's worth every one of them. Hike through beautiful scenery while hitting your daily step goal on this well-known route.

When you've finished up at this trekking route in Middlefield, visit some of the other attractions in and around the area. Glendale Falls isn't far from Skyline Trail and is recommended by travelers and locals alike.

Plan a trip to see Skyline Trail

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $541, price is now $405 per person
$405
per person
Dec 30 - Jan 2
found 22 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
18/10 Exceptional! (215 reviews)
Room spotless. However no cups in bathroom. Wine chiller did not work and had to be replaced. Also had to request clothing hangers for clothing. Only two hangers were in room.

Reviewed on Nov 9, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,017, price is now $756 per person
$756
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
7.4/10 Good! (549 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $753, price is now $568 per person
$568
per person
Dec 27 - Dec 31
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
17.6/10 Exceptional! (2,129 reviews)
Best of the Berkshires! Clean, Comfortable and convenient. Parking is a bit weird and cramped but not overshadowing the room itself.

Reviewed on Nov 10, 2025

Popular places to visit

A hidden treasure for sure

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
Had to wait on the light to get just right...totality worth it!!! #InStone

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
FairBridge Inn Express
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Berkshires Untold
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Quality Inn
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
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
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 Lenox MA
Howard Johnson by Wyndham Lenox
See all 1,726 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.

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