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.

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

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

A restaurant interior with white tables, cushioned booths, and a bar area.

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

SAR 385

SAR 430 total

includes taxes & fees

10 Nov - 11 Nov

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

A dining area with large windows, wooden furniture, and a view of a lake.

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.

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

19.2 km from Skyline Trail

Gustavo

SAR 408

SAR 456 total

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

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

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

3. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

James

SAR 348

SAR 388 total

includes taxes & fees

15 Nov - 16 Nov

A grassy area with a lake, trees, and red chairs arranged around a fire pit.

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 large bed, a modern headboard, a nightstand, a red cabinet, a window with blinds, and a view of greenery outside.

4. Berkshire Lake Lodge

13 km from Skyline Trail

mike

SAR 449

SAR 502 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A modern restaurant with wooden flooring, bar area, and seating arrangements.

5. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

SAR 471

SAR 527 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

6. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

SAR 412

SAR 460 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

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

19.3 km from Skyline Trail

Ginger

SAR 357

SAR 398 total

includes taxes & fees

24 Nov - 25 Nov

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

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

8. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

SAR 489

SAR 546 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

A spacious living room with a large sofa, a coffee table, and a fireplace.

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

SAR 445

SAR 498 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

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

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

11. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Michael

SAR 322

SAR 443 total

includes taxes & fees

22 Nov - 23 Nov

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

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

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

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

12. Chambery Inn

18.9 km from Skyline Trail

Alexandra

SAR 872

SAR 973 total

includes taxes & fees

3 Nov - 4 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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

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

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

SAR 297

SAR 331 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

14. 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 a large bed, a separate sitting area, a bathtub, and a large mirror.

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

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

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

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

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

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

A modern bathroom with a marble countertop, a round mirror, a black coffee machine, a microwave, and a black refrigerator.

16. Pilgrim Inn

18.5 km from Skyline Trail

james

SAR 301

SAR 336 total

includes taxes & fees

8 Nov - 9 Nov

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Top Skyline Trail Hotel Reviews

Chambery Inn

10/10 Excellent

"Super welcoming and charming inn."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Room was very clean and updated. We enjoyed the deck, although it needs some updating due to broken boards. I was told the restaurant was a fine place to dine. Desk staff was helpful."

Hotel On North

10/10 Excellent

"Perfect for our weekend family trip. Staff was super friendly. Walkable to multiple bakeries/cafes for breakfast. Walls are a little thin so noise can be a problem but otherwise no complaints."

Quality Inn Lee - Lenox South

8/10 Good

"Bed was comfortable, breakfast was fine, and it's a generally attractive property. We were in room 125, which was awkwardly laid out. The toilet was mashed up against the sink, and the desk was opposite the foot of the bed, making a traffic bottleneck. I'd guess 126 is the same, but hopefully the rest of the rooms weren't."

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

10/10 Excellent

"Really excellent spot for families. Loved having a townhouse to spread out and good kitchenette. Amenities were great and helped get little kids energy out."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"We enjoyed a delicious home cooked breakfast! The staff was wonderful and very accommodating. Lots of ideas were given to us as to where to visit in the area."

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

8/10 Good

"all good"

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 Whitlock

10/10 Excellent

"Nice location."

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 Yankee Inn

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

3. Quality Inn Lee - Lenox South

4. Berkshire Lake Lodge

5. Courtyard by Marriott Lenox Berkshires

6. Hampton Inn & Suites Berkshires-Lenox

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

8. Berkshires Untold

9. Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

11. Berkshire Mountain Lodge

12. Chambery Inn

13. Howard Johnson by Wyndham Lenox

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Top Skyline Trail Hotel Reviews

Chambery Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hotel On North

Quality Inn Lee - Lenox South

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

The Cornell Inn, Lenox & The Berkshires

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

Hampton Inn & Suites Berkshires-Lenox

The Whitlock

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