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13 Dec - 14 Dec
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19 Dec - 21 Dec
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Our top choices for Skyline Trail hotels

Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
19.8 km from Skyline Trail
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is 3.449.099 ₫
3.852.644 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
18.9 km from Skyline Trail
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
19.2 km from Skyline Trail
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is 4.900.353 ₫
5.747.379 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Lakehouse Inn
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
19.5 km from Skyline Trail
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is 2.714.882 ₫
3.032.523 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
19.4 km from Skyline Trail
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is 2.714.882 ₫
3.032.522 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
19.6 km from Skyline Trail
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is 1.969.409 ₫
2.199.829 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
19.3 km from Skyline Trail
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.974.006 ₫
3.321.965 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
19.2 km from Skyline Trail
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.664.495 ₫
2.976.241 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
19.9 km from Skyline Trail
9.2 out of 10, Wonderful, (590)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.551.445 ₫
3.966.965 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Courtyard by Marriott Lenox Berkshires
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
19.5 km from Skyline Trail
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is 2.596.107 ₫
3.487.549 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
19.8 km from Skyline Trail
9.0 out of 10, Wonderful, (815)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.884.484 ₫
3.221.968 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Berkshires Untold
Front of property
Becket Motel

Becket Motel

Becket Motel
2.5 star property
11.3 km from Skyline Trail
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
The price is 2.551.779 ₫
3.731.885 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Becket Motel
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
18.6 km from Skyline Trail
8.4 out of 10, Very good, (1002)
"Room was clean and comfortable; location was good with a breakfast restaurant next door. The in-house breakfast was OK, but we preferred an upgrade. Receptionist staff member was professional and pleasant. "
United States
Patrick
The price is 2.330.011 ₫
2.602.623 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
18.6 km from Skyline Trail
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is 2.367.630 ₫
2.644.643 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Sunset Inn
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
19.5 km from Skyline Trail
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is 2.078.253 ₫
2.321.330 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
18 km from Skyline Trail
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is 2.107.191 ₫
2.353.733 ₫ total
includes taxes & fees
27 Dec - 28 Dec
FairBridge Inn Express
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.
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Top Skyline Trail Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Comfortable, quiet, clean, great breakfast "
Elizabeth 3-night trip
Posted 6 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Element Lenox Berkshires

Element Lenox Berkshires

10/10 Excellent
"Very clean and updated rooms. Easy to get around without being in a heavy commercial area. Parking easy. Staff friendly and helpful. Good breakfast as well!"
Lynn 1-night trip
Posted 1 month ago
Element Lenox Berkshires

Hotels near other Skyline Trail attractions

Glendale Falls

Commune with nature and explore the great outdoors at Glendale Falls during your travels in Huntington. Wander the lakeside in this relaxing area.
See properties

Kushi Institute

Enjoy the student vibe at Kushi Institute as part of your travels around Becket. Discover the area's entertainment venues or seek out its hiking trails.
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Frequently asked questions

What's the area like around Skyline Trail?
Skyline Trail is located in a welcoming area of Middlefield known for its beautiful lakeside setting and cosy cafes. You'll find 12 hotels and other accommodations within a few miles for a convenient home base.
How many hotels are there close to Skyline Trail?
Expedia has 12 hotels and other accommodation options a few miles from Skyline Trail.
If I need to cancel the hotel reservation for my stay near Skyline Trail, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to view top deals close to Skyline Trail.

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