
Hotels near Skyline Trail Middlefield
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Where to stay near Skyline Trail?




9.8 out of 10, Exceptional, (13)
9.8/10
Exceptional
(13)
The price is $135
$135
$151 total
includes taxes & fees
Jan 4 - Jan 5, 2026




9.6 out of 10, Exceptional, (373)
9.6/10
Exceptional
(373)
The price is $190
$190
$212 total
includes taxes & fees
Dec 21 - Dec 22




Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield3.0 star property
19.4 km from Skyline Trail
9.2 out of 10, Wonderful, (658)
9.2/10
Wonderful
(658)
The price is $128
$128
$143 total
includes taxes & fees
Jan 2 - Jan 3, 2026




Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires3.0 star property
19.9 km from Skyline Trail
9.2 out of 10, Wonderful, (591)
9.2/10
Wonderful
(591)
The price is $139
$139
$155 total
includes taxes & fees
Dec 22 - Dec 23




Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox2.5 star property
19.5 km from Skyline Trail
9.2 out of 10, Wonderful, (1000)
9.2/10
Wonderful
(1000)
The price is $105
$105
$117 total
includes taxes & fees
Jan 4 - Jan 5, 2026




9.0 out of 10, Wonderful, (817)
9.0/10
Wonderful
(817)
The price is $110
$110
$123 total
includes taxes & fees
Dec 21 - Dec 22




The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
19.2 km from Skyline Trail
9.0 out of 10, Wonderful, (1003)
9.0/10
Wonderful
(1003)
The price is $100
$100
$112 total
includes taxes & fees
Jan 8 - Jan 9, 2026




The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham2.5 star property
19.6 km from Skyline Trail
9.2 out of 10, Wonderful, (1000)
9.2/10
Wonderful
(1000)
The price is $80
$80
$89 total
includes taxes & fees
Dec 21 - Dec 22




9.0 out of 10, Wonderful, (792)
9.0/10
Wonderful
(792)
The price is $88
$88
$120 total
includes taxes & fees
Jan 18 - Jan 19, 2026




Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South2.5 star property
18.6 km from Skyline Trail
8.4 out of 10, Very Good, (1001)
8.4/10
Very Good
(1001)
The price is $83
$83
$92 total
includes taxes & fees
Jan 11 - Jan 12, 2026




7.6 out of 10, Good, (410)
7.6/10
Good
(410)
The price is $90
$90
$101 total
includes taxes & fees
Dec 21 - Dec 22




Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox2.0 star property
19.5 km from Skyline Trail
7.6 out of 10, Good, (828)
7.6/10
Good
(828)
The price is $79
$79
$88 total
includes taxes & fees
Dec 21 - Dec 22




Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG2.5 star property
19.3 km from Skyline Trail
9.2 out of 10, Wonderful, (65)
9.2/10
Wonderful
(65)
The price is $113
$113
$126 total
includes taxes & fees
Dec 21 - Dec 22




5.8 out of 10, (332)
5.8/10
(332)
The price is $80
$80
$89 total
includes taxes & fees
Jan 2 - Jan 3, 2026




5.4 out of 10, (810)
5.4/10
(810)
The price is $89
$89
$99 total
includes taxes & fees
Dec 21 - Dec 22
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.
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.