Search Hotels Near Skyline Trail, Middlefield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Jan - 3 Jan
Tomorrow
3 Jan - 4 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Skyline Trail hotels

Lobby
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 ฿1,677
฿1,873 total
includes taxes & fees
1 Feb - 2 Feb
Pilgrim Inn
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 ฿2,525
฿2,820 total
includes taxes & fees
15 Jan - 16 Jan
FairBridge Inn Express
Exterior
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, (1003)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ฿3,273
฿3,656 total
includes taxes & fees
11 Jan - 12 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (1005)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ฿3,188
฿3,561 total
includes taxes & fees
11 Jan - 12 Jan
The Yankee, Trademark Collection by Wyndham
Exterior
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)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is ฿4,255
฿4,753 total
includes taxes & fees
8 Jan - 9 Jan
Element Lenox Berkshires
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 ฿5,800
฿6,802 total
includes taxes & fees
16 Jan - 17 Jan
Lakehouse Inn
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)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ฿2,593
฿2,897 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
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, (374)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
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, (1001)
"Very comfortable beds! "
United States
Gerald
The price is ฿3,451
฿3,854 total
includes taxes & fees
4 Jan - 5 Jan
Hampton Inn & Suites Berkshires-Lenox
Fridge, microwave, stovetop, dishwasher
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, (801)
"great stall and friendly pet friendly place"
United States
bonnie
The price is ฿3,110
฿4,178 total
includes taxes & fees
11 Jan - 12 Jan
Berkshire Mountain Lodge
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
19.8 km from Skyline Trail
9.0 out of 10, Wonderful, (825)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is ฿3,992
฿4,459 total
includes taxes & fees
4 Jan - 5 Jan
Berkshires Untold
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, (660)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ฿4,039
฿4,511 total
includes taxes & fees
9 Jan - 10 Jan
Hilton Garden Inn Lenox Pittsfield
Lobby sitting area
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, (71)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is ฿3,863
฿4,315 total
includes taxes & fees
4 Jan - 5 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
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, (594)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ฿4,381
฿4,894 total
includes taxes & fees
6 Jan - 7 Jan
Courtyard by Marriott Lenox Berkshires
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, (411)
"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 ฿2,837
฿3,169 total
includes taxes & fees
3 Jan - 4 Jan
Sunset Inn
Exterior
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 ฿2,490
฿2,781 total
includes taxes & fees
4 Jan - 5 Jan
Howard Johnson by Wyndham Lenox
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.
View all properties

Top Skyline Trail Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"The room was spotless, staff was friendly, and the facility was extremely clean. If in the area we will definately stay here again."
Michelle 1-night trip
Posted 4 days 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.
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.
See properties

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.
Where is the best place to stay near Skyline Trail?
The Yankee, Trademark Collection by Wyndham is one of the top choices for your stay based on our traveller 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 options in the area include Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
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.