Hotels near Skyline Trail
Search over 1,744 hotels from $67
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Tomorrow night
Check prices close to Skyline Trail for tomorrow night, Jun 27 - Jun 28Featured Hotels near Skyline Trail

FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
11.18 mi from Skyline Trail
$60 nightly
The price is $67 total per night
$67 total
Jun 28 - Jun 29
Total with taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi

Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Free Cancellation
Reserve now, pay when you stay
11.54 mi from Skyline Trail
$135 nightly
The price is $151 total per night
$151 total
Jul 27 - Jul 28
Total with taxes and fees
At Quality Inn Lee - Lenox South, guests have access to free WiFi in public areas, express check-in, and express check-out. Onsite parking is offered for a fee. The front desk is staffed 24/7 to help with tours or tickets, and answer any questions about the accommodations. This hotel also has free newspapers.
Breakfast included
Free WiFi

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
11.9 mi from Skyline Trail
$178 nightly
The price is $198 total per night
$198 total
Jul 1 - Jul 2
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Free Cancellation
12.01 mi from Skyline Trail
$165 nightly
The price is $184 total per night
$184 total
Jul 7 - Jul 8
Total with taxes and fees
At Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with concierge services and securing valuables. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.11 mi from Skyline Trail
$159 nightly
The price is $177 total per night
$177 total
Jun 29 - Jun 30
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff standing by 24 hours a day to assist with luggage storage and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
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
$162 nightly
The price is $181 total per night
$181 total
Jul 26 - Jul 27
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub

The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.17 mi from Skyline Trail
$127 nightly
The price is $142 total per night
$142 total
Jul 9 - Jul 10
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.27 mi from Skyline Trail
$159 nightly
The price is $178 total per night
$178 total
Jun 29 - Jun 30
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
12.66 mi from Skyline Trail
$249 nightly
The price is $278 total per night
$278 total
Jul 7 - Jul 8
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, an ATM, and a banquet hall.
Pet friendly
Parking included
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 | 1,744 hotels |
|---|---|
Lowest Price | $67 |
Highest Price | $278 |
Popular hotels | The Yankee Inn, Berkshire Mountain Lodge, Quality Inn Lee - Lenox South, FairBridge Inn Express, Berkshires Untold, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox, Hotel On North |
Recent Reviews

Quality Inn Lee - Lenox South
5/5 Excellent
"Very clean au"
A verified traveler stayed at Quality Inn Lee - Lenox South
Posted 2 hours ago
More to Explore
More to Explore
- 5 Star Hotels in Norwich Lake
- 5 Star Hotels in Hinsdale
- Apartments in Hinsdale
- B&B in Hinsdale
- Cheap Hotels in Hinsdale
- Hotels with Pool in Hinsdale
- Romantic Getaways & Hotels in Hinsdale
- Hinsdale Hotels
- Inns in Hinsdale
- Vacation Homes in Hinsdale
- Resorts in Hinsdale
- Hotels near Chester Town Hall
- Hotels near Jacob's Pillow
- B&B in Worthington
- Cottages in Worthington
- Guest Houses in Worthington
- Worthington Hotels
- Inns in Worthington
- Motels in Worthington
- Cabin Rentals in Western Massachusetts
- Cottages in Western Massachusetts
- Extended Stay Hotels in Western Massachusetts
- Boutique Hotels in Western Massachusetts
- Cheap Hotels in Western Massachusetts
- Kid Friendly Hotels in Western Massachusetts
- Golf Resorts & in Western Massachusetts
- Hotels with Hot Tubs in Western Massachusetts
- Romantic Getaways & Hotels in Western Massachusetts
- Spa Resorts & in Western Massachusetts
- Plainfield Hotels
- Hotels near Lee Premium Outlets
- Otis Hotels
- Hotels near Littleville Lake
- Hotels near Crane Museum of Papermaking
- Hotels near Canoe Meadows Wildlife Sanctuary
- Lenox Hotels
- Hotels near Pyramid Lake
- Farmstay in Chester
- Apartments in Chester
- Pet Friendly Hotels in Chester
- Chester Hotels
- Motels in Chester
- Hotels near Chesterfield Gorge
- Hotels near Kennedy Park
- Hotels near Otis Ridge
- 4 Star Hotels in Cummington
- Cabin Rentals in Cummington
- Pet Friendly Hotels in Cummington
- Cummington Hotels
- Inns in Cummington
- Lodges in Cummington
- Hotels near Berkshire Mountain Country Store
- Hotels near Becket Land Trust Historic Quarry
- Hotels near Glendale Falls
- Inns in Washington
- 5 Star Hotels in Becket
- Farmstay in Becket
- Apartments in Becket
- Cabin Rentals in Becket
- Condo Rentals in Becket
- Cottages in Becket
- Guest Houses in Becket
- Beach Resorts & in Becket
- Cheap Hotels in Becket
- Kid Friendly Hotels in Becket
- Hotels with Pool in Becket
- Hotels with Restaurants in Becket
- Pet Friendly Hotels in Becket
- Romantic Getaways & Hotels in Becket
- Ski Resorts & in Becket
- Becket Hotels
- Lodges in Becket
- Motels in Becket
- Rv Parks in Becket
- Resorts in Becket
- Middlefield Hotels
- 5 Star Hotels in Dalton
- Cabin Rentals in Dalton
- Dalton Hotels
- Motels in Dalton
- Vacation Homes in Dalton
- Resorts in Dalton
- Cabin Rentals in Windsor
- Cottages in Windsor
- Windsor Hotels
- Inns in Windsor
- Lee Hotels
- Hotels near Animagic Museum of Animation
- Hotels near Herman Melville's Arrowhead
- Hotels near Berkshire Athenaeum
- Hotels near Guido's Marketplace
- Cabin Rentals in Chesterfield
- Hotels near Berkshire Scenic Railway Museum


