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23 Dec - 24 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Skyline Trail hotels

Individually decorated, individually furnished, desk, laptop workspace
Pilgrim Inn

Pilgrim Inn

Pilgrim Inn
2.5 star property
18.5 km from Skyline Trail
5.8 out of 10, (332)
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is 2.107.831 ₫
2.354.447 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Pilgrim Inn
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, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is 1.990.730 ₫
2.223.645 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
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, (811)
"Room spotless and staff helpful."
United States
William
The price is 2.107.831 ₫
2.354.447 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
FairBridge Inn Express
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 2.736.760 ₫
3.056.962 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
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, (1007)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is 2.641.200 ₫
2.950.221 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
19.8 km from Skyline Trail
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is 3.552.525 ₫
3.968.170 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Element 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, (794)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is 2.596.896 ₫
3.488.609 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
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
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, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is 3.365.162 ₫
3.758.834 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield
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, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.660.287 ₫
4.088.540 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Courtyard by Marriott Lenox Berkshires
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, (1003)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is 2.175.198 ₫
2.429.696 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn Lee - Lenox South
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
19.8 km from Skyline Trail
9.0 out of 10, Wonderful, (819)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.887.334 ₫
3.225.152 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Berkshires Untold
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, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is 2.974.911 ₫
3.322.974 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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 2.078.885 ₫
2.322.036 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Howard Johnson by Wyndham Lenox
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 2.368.350 ₫
2.645.447 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Sunset Inn
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

Element Lenox Berkshires

Element Lenox Berkshires

10/10 Excellent
"Excellent location, clean, comfortable. Staff was friendly, the only issue was that we got to breakfast an hour before it ended and there were no eggs other protein or much more than a fee bagels and yogurt. This was informed tonus by the person tending the breakfast area while ahe stood next to still hot griddle. She didn’t offer any alternative. It feels like poor planning. Other than that, it was great."
Eunice 1-night trip
Posted 7 days ago
Element Lenox Berkshires
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 2 weeks ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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.
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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.