Book a hotel near Skyline Trail, Middlefield
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Top hotels close to Skyline Trail

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
11.18 mi from Skyline Trail
$75 nightly
The price is $84 total per night
$84 total
Nov 16 - Nov 17
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi

Quality Inn
170 Housatonic Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
11.53 mi from Skyline Trail
$87 nightly
The price is $98 total per night
$98 total
Dec 1 - Dec 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. A restaurant, a 24-hour front desk, and express check-out are also provided.
Breakfast included
Free WiFi

Chambery Inn
199 Main St, Lee, MA
11.76 mi from Skyline Trail
$190 nightly
The price is $212 total per night
$212 total
Nov 16 - Nov 17
Total with taxes and fees
A hot tub, free self parking, and free newspapers are featured at this bed & breakfast. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Hot Tub
Spa

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St, Lee, MA
Free Cancellation
11.9 mi from Skyline Trail
$110 nightly
The price is $122 total per night
$122 total
Dec 3 - Dec 4
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
Breakfast included
Pet friendly

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street, Pittsfield, MA
Free Cancellation
12.01 mi from Skyline Trail
$110 nightly
The price is $122 total per night
$122 total
Dec 4 - Dec 5
Total with taxes and fees
This hotel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, laundry facilities, and concierge services are also on offer.
Pool
Hot Tub

Hilton Garden Inn Lenox Pittsfield
1032 South Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
12.05 mi from Skyline Trail
$111 nightly
The price is $124 total per night
$124 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.
Pool
Pet friendly

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.09 mi from Skyline Trail
$79 nightly
The price is $88 total per night
$88 total
Nov 14 - Nov 15
Total with taxes and fees
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Pool
Parking included

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.11 mi from Skyline Trail
$111 nightly
The price is $124 total per night
$124 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
12.12 mi from Skyline Trail
$120 nightly
The price is $135 total per night
$135 total
Nov 16 - Nov 17
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.17 mi from Skyline Trail
$100 nightly
The price is $112 total per night
$112 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.27 mi from Skyline Trail
$94 nightly
The price is $105 total per night
$105 total
Nov 16 - Nov 17
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
12.62 mi from Skyline Trail
$88 nightly
The price is $99 total per night
$99 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
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.
Skyline Trail hotels essential information
Accommodation | 1,724 hotels |
|---|---|
Lowest Price | $84 |
Highest Price | $212 |
Popular hotels | Berkshire Mountain Lodge, FairBridge Inn Express, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Berkshires Untold, Quality Inn, The Yankee, Trademark Collection by Wyndham, Hampton Inn & Suites Berkshires-Lenox, Howard Johnson by Wyndham Lenox, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, Hilton Garden Inn Lenox Pittsfield, Chambery Inn |
Recent Skyline Trail hotel reviews by fellow wanderers

Berkshires Untold
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."
A verified traveler stayed at Berkshires Untold





