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 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.

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

AED 355

AED 396 total

includes taxes & fees

20 Nov - 21 Nov

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

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

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.

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

19.2 km from Skyline Trail

Gustavo

AED 400

AED 446 total

includes taxes & fees

22 Nov - 23 Nov

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

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

AED 340

AED 380 total

includes taxes & fees

15 Nov - 16 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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

19.3 km from Skyline Trail

Ginger

AED 349

AED 390 total

includes taxes & fees

24 Nov - 25 Nov

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

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

5. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

AED 436

AED 487 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

6. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 476

AED 532 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

7. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Joel

AED 315

AED 434 total

includes taxes & fees

22 Nov - 23 Nov

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

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

8. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

AED 403

AED 450 total

includes taxes & fees

30 Oct - 31 Oct

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

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

9. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

AED 461

AED 515 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 modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

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

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Francis

AED 511

AED 570 total

includes taxes & fees

1 Nov - 2 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, 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.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

11. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

AED 290

AED 324 total

includes taxes & fees

25 Oct - 26 Oct

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

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

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

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

12. Sunset Inn

18.6 km from Skyline Trail

Lauren

AED 298

AED 332 total

includes taxes & fees

1 Nov - 2 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 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.

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

AED 853

AED 953 total

includes taxes & fees

1 Nov - 2 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 modern bathroom with a marble countertop, a round mirror, a black coffee machine, a microwave, and a black refrigerator.

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

14. Pilgrim Inn

18.5 km from Skyline Trail

james

AED 294

AED 329 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

15. FairBridge Inn Express

18 km from Skyline Trail

Richard

AED 245

AED 274 total

includes taxes & fees

8 Nov - 9 Nov

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Compare popular hotels close to Skyline Trail

Property	Property class	Guest rating
The Yankee Inn	9.2 Wonderful 1,003 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,007 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,005 reviews	View
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG	9.2 Wonderful 244 reviews	View
Hilton Garden Inn Lenox Pittsfield	9.2 Wonderful 715 reviews	View

Top Skyline Trail Hotel Reviews

Berkshires Untold

10/10 Excellent

"Berkshires Untold is THE PLACE to stay in Lenox. The rooms are terrific. They've been beautifully upgraded and the bathrooms are big and as nice as can be. We were concerned about the noise from the cars on Rte 7 as our room faced the street, but it was not an issue whatsoever. The breakfasts were just right. Coffee was plentiful and ready in the morning when we got up. And the owners (or managers) are suburb; they handled a problem I had with such grace and so generously I was astounded! Bottom line: next time we return for a Foliage experience, we're coming back to the Berkshires Untold!"

Berkshire Mountain Lodge

10/10 Excellent

"Wonderful place to stay for short or long time. Everything is just perfect."

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"

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."

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

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.

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 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 AED 274

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Treat yourself

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

5. Hilton Garden Inn Lenox Pittsfield

6. Berkshire Lake Lodge

7. Berkshire Mountain Lodge

8. Hampton Inn & Suites Berkshires-Lenox

9. Courtyard by Marriott Lenox Berkshires

10. Element by Marriott Lenox Berkshires

11. Howard Johnson by Wyndham Lenox

12. Sunset Inn

13. Chambery Inn

14. Pilgrim Inn

15. FairBridge Inn Express

Compare popular hotels close to Skyline Trail

Top Skyline Trail Hotel Reviews

Berkshires Untold

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

The Yankee Inn

Quality Inn Lee - Lenox South

The Whitlock

Chambery Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hotel On North

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