Skyline Trail

Plan a trip to see Skyline Trail

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was £764, price is now £620 per person
£620
per person
14 Oct - 20 Oct
found 1 day ago
Return flight included
London (LHR) to Albany (ALB)
8.8/10 Excellent! (2,598 reviews)

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
Price was £1,134, price is now £955 per person
£955
per person
14 Oct - 20 Oct
found 1 day ago
Return flight included
London (LHR) to Albany (ALB)
9.4/10 Exceptional! (501 reviews)
I really loved the history of the Porches & the proximity to Mass MoCA which is a short walk to the amazing museum! Everything about it is charming!

Reviewed on 6 Sept 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was £829, price is now £710 per person
£710
per person
14 Oct - 20 Oct
found 1 day ago
Return flight included
London (LHR) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
The website differs from the actual room I was in, and Expedia way overcharged us.

Reviewed on 7 Sept 2026

Stay near popular Skyline Trail attractions

Skyline Trail

You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside or simply savour its cosy cafes.
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Top Hotel Deals

FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
FairBridge Inn Express
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The Yankee Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
Quality Inn Lee - Lenox South
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
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 1,757 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.