Book a hotel near Skyline Trail, Middlefield
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top hotels close to Skyline Trail
Pilgrim Inn
165 Housatonic St Lee MA
Free Cancellation
Reserve now, pay when you stay
11.49 mi from Skyline Trail
$49 nightly
The price is $55 total per night
$55 total
Feb 3 - Feb 4
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Chambery Inn
199 Main St Lee MA
11.76 mi from Skyline Trail
$190 nightly
The price is $212 total per night
$212 total
Jan 13 - Jan 14
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
$98 nightly
The price is $109 total per night
$109 total
Feb 1 - Feb 2
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
Lakehouse Inn
615 Laurel St. Lee MA
11.94 mi from Skyline Trail
$139 nightly
The price is $155 total per night
$155 total
Jan 18 - Jan 19
Total with taxes and fees
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a snack bar/deli, and a picnic area are also on offer.
Breakfast included
Parking included
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street Pittsfield MA
Free Cancellation
12.01 mi from Skyline Trail
$123 nightly
The price is $137 total per night
$137 total
Jan 25 - Jan 26
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
$128 nightly
The price is $143 total per night
$143 total
Jan 23 - Jan 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
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
Jan 25 - Jan 26
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
$108 nightly
The price is $120 total per night
$120 total
Feb 10 - Feb 11
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
$101 nightly
The price is $113 total per night
$113 total
Jan 19 - Jan 20
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
$122 nightly
The price is $136 total per night
$136 total
Jan 13 - Jan 14
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
Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.33 mi from Skyline Trail
$148 nightly
The price is $165 total per night
$165 total
Jan 21 - Jan 22
Total with 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
$98 nightly
The price is $109 total per night
$109 total
Jan 23 - Jan 24
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 | 1,715 hotels |
|---|---|
Lowest Price | $55 |
Highest Price | $212 |
Popular hotels | Berkshire Mountain Lodge, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Pilgrim Inn, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, Courtyard by Marriott Lenox Berkshires, Chambery Inn, Hilton Garden Inn Lenox Pittsfield, Lakehouse Inn |
Recent Skyline Trail hotel reviews by fellow wanderers
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Everything was great! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
