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
$69 nightly
The price is $78 total per night
$78 total
Aug 20 - Aug 21
Total includes 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
$135 nightly
The price is $151 total per night
$151 total
Aug 6 - Aug 7
Total includes 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
$250 nightly
The price is $279 total per night
$279 total
Jul 30 - Jul 31
Total includes 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, Ascend Hotel Collection
435 Laurel St, Lee, MA
Free Cancellation
Reserve now, pay when you stay
11.9 mi from Skyline Trail
$195 nightly
The price is $217 total per night
$217 total
Jul 30 - Jul 31
Total includes 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

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
$99 nightly
The price is $111 total per night
$111 total
Jul 27 - Jul 28
Total includes 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.

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.11 mi from Skyline Trail
$161 nightly
The price is $180 total per night
$180 total
Jul 30 - Jul 31
Total includes 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
$121 nightly
The price is $135 total per night
$135 total
Jul 30 - Jul 31
Total includes 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.

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
$135 nightly
The price is $151 total per night
$151 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and 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
$199 nightly
The price is $222 total per night
$222 total
Jul 27 - Jul 28
Total includes 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

Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.33 mi from Skyline Trail
$203 nightly
The price is $227 total per night
$227 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
12.62 mi from Skyline Trail
$129 nightly
The price is $144 total per night
$144 total
Jul 27 - Jul 28
Total includes 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

The Constance by the Lenox Collection
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
12.83 mi from Skyline Trail
$185 nightly
The price is $206 total per night
$206 total
Aug 13 - Aug 14
Total includes taxes and fees
A gym, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A library, express check-out, and wedding services are also on offer.
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 | 1,735 hotels |
---|---|
Lowest Price | $78 |
Highest Price | $279 |
Popular hotels | FairBridge Inn Express, Quality Inn, Berkshires Untold, Berkshire Mountain Lodge, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Howard Johnson by Wyndham Lenox, Hampton Inn & Suites Berkshires-Lenox, Courtyard by Marriott Lenox Berkshires, Chambery Inn, The Constance by the Lenox Collection |
Recent Skyline Trail hotel reviews by fellow wanderers

The Constance by the Lenox Collection
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Easy walk to town. Plenty of restaurants available. "
A verified traveler stayed at The Constance by the Lenox Collection
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