The Best Hotels Closest to Skyline Trail in Middlefield for 2026

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Our top choices for Skyline Trail hotels

Two Adirondack chairs facing a river with a forested hill in the background.

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

SAR 472 total

includes taxes & fees

6 Dec - 7 Dec

A calm lake at dusk with a wooden dock and two chairs facing the water.

2. Berkshire Lake Lodge

13 km from Skyline Trail

mike

SAR 457 total

includes taxes & fees

6 Nov - 7 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

19.2 km from Skyline Trail

Gustavo

SAR 456 total

includes taxes & fees

3 Dec - 4 Dec

4. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

James

SAR 356 total

includes taxes & fees

2 Dec - 3 Dec

An indoor swimming pool with clear water, tiled floors, and a blue wall.

5. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

19.3 km from Skyline Trail

Ruth

SAR 415 total

includes taxes & fees

4 Dec - 5 Dec

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

6. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

SAR 527 total

includes taxes & fees

15 Nov - 16 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

7. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

SAR 460 total

includes taxes & fees

11 Nov - 12 Nov

8. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Charline

SAR 406 total

includes taxes & fees

6 Dec - 7 Dec

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

SAR 498 total

includes taxes & fees

15 Nov - 16 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

10. Berkshires Untold

19.8 km from Skyline Trail

Brian

SAR 512 total

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

11. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Francis

SAR 566 total

includes taxes & fees

11 Nov - 12 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

12. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

SAR 331 total

includes taxes & fees

8 Nov - 9 Nov

A two-story building with a sign reading "Chambéry Inn".

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

SAR 777 total

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with a fenced area, lounge chairs, and a warning sign.

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

SAR 340 total

includes taxes & fees

6 Nov - 7 Nov

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

15. FairBridge Inn Express

18 km from Skyline Trail

William

SAR 298 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with two beds, a nightstand, a lamp, and a patterned floor.

16. Pilgrim Inn

18.5 km from Skyline Trail

james

SAR 336 total

includes taxes & fees

18 Nov - 19 Nov

View all properties

Other attractions near Skyline Trail

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

Top Skyline Trail Hotel Reviews

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Chambery Inn

Lee

10/10 Excellent

Elaine

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

t

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

Quality Inn Lee - Lenox South

Lee

10/10 Excellent

Anonymous traveler

Sunset Inn

Lee

10/10 Excellent

Patricia

Howard Johnson by Wyndham Lenox

Lenox

10/10 Excellent

Anonymous traveler

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

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 15 hotels and other accommodations within a few miles for a convenient home base.

What's the best hotel to stay near Skyline Trail?

Berkshire Mountain Lodge is one of the top choices for your stay based on our traveler data, and this aparthotel offers an indoor pool and free parking. You'll find it 12.1 mi (19.5 km) from Skyline Trail. Other good choices in the area include FairBridge Inn Express and The Yankee Inn.

How many hotels can I expect to find close to Skyline Trail?

Expedia has 15 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.

Find hotels near Skyline Trail, Middlefield from SAR 288

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

2. Berkshire Lake Lodge

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

4. Quality Inn Lee - Lenox South

5. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

6. Courtyard by Marriott Lenox Berkshires

7. Hampton Inn & Suites Berkshires-Lenox

8. Berkshire Mountain Lodge

9. Hilton Garden Inn Lenox Pittsfield

10. Berkshires Untold

11. Element by Marriott Lenox Berkshires

12. Howard Johnson by Wyndham Lenox

13. Chambery Inn

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Other attractions near Skyline Trail

Glendale Falls

Top Skyline Trail Hotel Reviews

Devonfield Inn B&B

10/10 Excellent

Frequently Asked Questions

What's the area like around Skyline Trail?

What's the best hotel to stay near Skyline Trail?

How many hotels can I expect to find close to Skyline Trail?

If I need to cancel the hotel reservation for my stay near Skyline Trail, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Skyline Trail?