Find hotels near Skyline Trail, Middlefield from ¥13,331

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Our top choices for Skyline Trail hotels

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

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 ¥21,182
¥23,660 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Element Lenox Berkshires

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 ¥11,934
¥13,331 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Yankee, Trademark Collection by Wyndham

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 ¥16,406
¥18,326 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Berkshires-Lenox

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 ¥20,064
¥22,411 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Lenox Pittsfield

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 ¥17,834
¥19,921 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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 ¥21,809
¥24,361 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox Berkshires

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 ¥15,822
¥17,673 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 ¥15,484
¥20,801 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Berkshire Mountain Lodge

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 ¥17,297
¥19,321 total
includes taxes & fees
Dec 24 - Dec 25
Berkshires Untold

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 ¥12,963
¥14,480 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Lee - Lenox South

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 ¥14,121
¥15,773 total
includes taxes & fees
Dec 25 - Dec 26
Sunset Inn

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 ¥12,395
¥13,845 total
includes taxes & fees
Dec 30 - Dec 31
Howard Johnson by Wyndham Lenox

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 ¥12,568
¥14,038 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Pilgrim Inn

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 ¥12,568
¥14,038 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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.

Top Skyline Trail Hotel Reviews

Hotels near other Skyline Trail attractions

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 cozy coffeehouses. You'll find 11 hotels and other accommodations within a few miles for a convenient home base.
What's the best hotel to stay near Skyline Trail?
The Yankee, Trademark Collection by Wyndham is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. You'll find it 12.2 mi (19.6 km) from Skyline Trail. Other good choices in the area include Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
How many hotels can I expect to find close to Skyline Trail?
Expedia has 11 hotels and other accommodations 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, most hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Plug in your dates, click on "Search", then use the filter option "fully refundable" to review the best deals available near Skyline Trail.
Where can I learn more about changing or cancelling my trip in the area near Skyline Trail?
For more information about picking new dates or cancelling your stay near Skyline Trail, head over to our customer service page.