The Best Hotels Closest to Skyline Trail in Middlefield for 2026

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Our top choices for Skyline Trail hotels

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

A lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

19.2 km from Skyline Trail

Gustavo

SAR 431

SAR 481 total

includes taxes & fees

15 Nov - 16 Nov

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

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A lodge with a large lawn, outdoor seating, and a dock.

A bedroom with a bed, a desk, a chair, a television, and a wardrobe.

2. Berkshire Lake Lodge

13 km from Skyline Trail

mike

SAR 477

SAR 532 total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

3. The Yankee Inn

19.6 km from Skyline Trail

Basil

SAR 334

SAR 373 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

4. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Lucinda

SAR 348

SAR 388 total

includes taxes & fees

12 Nov - 13 Nov

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

A hotel room with a wooden desk, a flat-screen TV, a coffee maker, a blue chair, and a lamp.

5. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

SAR 412

SAR 460 total

includes taxes & fees

30 Oct - 31 Oct

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

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A hotel patio with outdoor seating and a fire pit.

A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.

6. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

SAR 446

SAR 498 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A spacious lobby with a fireplace, seating area, and a bar.

7. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Joel

SAR 322

SAR 443 total

includes taxes & fees

22 Nov - 23 Nov

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

A snack bar with shelves of snacks and a refrigerated display.

A modern cafe with a counter, seating area, and large windows.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

19.3 km from Skyline Trail

Ginger

SAR 372

SAR 415 total

includes taxes & fees

22 Nov - 23 Nov

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A covered outdoor area with stone pillars and a view of a road and green hills.

9. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

SAR 472

SAR 527 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

An outdoor seating area with Adirondack chairs and a fire feature.

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Francis

SAR 507

SAR 566 total

includes taxes & fees

8 Nov - 9 Nov

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

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

11. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

SAR 296

SAR 331 total

includes taxes & fees

25 Oct - 26 Oct

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

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.

12. Chambery Inn

18.9 km from Skyline Trail

Alexandra

SAR 872

SAR 974 total

includes taxes & fees

3 Nov - 4 Nov

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

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

A hotel room with two beds, a chair, and a bedside table with a phone.

13. Sunset Inn

18.6 km from Skyline Trail

Lauren

SAR 304

SAR 340 total

includes taxes & fees

2 Nov - 3 Nov

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

A well-lit dining area with a round table and chairs, a potted plant, and a view through large windows.

A white building with a red awning and a sign that reads "PILGRIM INN" with amenities listed.

A modern bathroom with a marble vanity, a round mirror, a flat-screen TV, a microwave, and an air conditioning unit.

14. Pilgrim Inn

18.5 km from Skyline Trail

james

SAR 301

SAR 336 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.

A dining area with wooden tables and chairs, a television, and a door with a sign.

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

A hotel room with a desk, computer, TV, and a chair.

15. FairBridge Inn Express

18 km from Skyline Trail

Richard

SAR 243

SAR 271 total

includes taxes & fees

8 Nov - 9 Nov

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Top Skyline Trail Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

Quality Inn Lee - Lenox South

10/10 Excellent

"A"

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

The Whitlock

10/10 Excellent

"Nice location."

Chambery Inn

10/10 Excellent

"The property is amazing, specially for a romantic visit."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Check in & out were easy. Mint restaurant was GREAT. View from the balcony overlooking the lake was super. Same weekend for the last four years & we will be back."

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.

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Becket Arts Center

Enjoy an outing to Becket Arts Center during your stay in Becket. Wander the lakeside in this relaxing area.

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Fox Den Wildlife Management Area

You can take time to visit Fox Den Wildlife Management Area during your travels to Worthington. Make some time to visit the shops while you're in the area.

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Iroquis Waterfront

Why not spend a lazy afternoon at Iroquis Waterfront during your trip to Becket? Wander the lakeside in this relaxing area.

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Ashmere Lake

Commune with nature and explore the great outdoors at Ashmere Lake during your travels in Hinsdale. Make some time to visit the shops while you're in the area.

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Hiram H. Fox Wildlife Management Area

You can take time to visit Hiram H. Fox Wildlife Management Area during your travels to Huntington. While you're in the area, stroll along the lakeside.

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Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.

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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 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 271

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Our top choices for Skyline Trail hotels

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

2. Berkshire Lake Lodge

3. The Yankee Inn

4. Quality Inn Lee - Lenox South

5. Hampton Inn & Suites Berkshires-Lenox

6. Hilton Garden Inn Lenox Pittsfield

7. Berkshire Mountain Lodge

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

9. Courtyard by Marriott Lenox Berkshires

10. Element by Marriott Lenox Berkshires

11. Howard Johnson by Wyndham Lenox

12. Chambery Inn

13. Sunset Inn

14. Pilgrim Inn

15. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

The Cornell Inn, Lenox & The Berkshires

The Yankee Inn

Quality Inn Lee - Lenox South

Berkshires Untold

Berkshire Mountain Lodge

The Whitlock

Chambery Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Other attractions near Skyline Trail

Glendale Falls

Becket Arts Center

Fox Den Wildlife Management Area

Iroquis Waterfront

Ashmere Lake

Hiram H. Fox Wildlife Management Area

Chester Town Hall

Frequently asked questions