The Best Hotels Closest to Skyline Trail in Middlefield for 2026

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Our top choices for Skyline Trail hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

19.6 km from Skyline Trail

William

AED 389

AED 435 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

2. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

AED 403

AED 450 total

includes taxes & fees

25 Oct - 26 Oct

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

A room with two beds, a round mirror, a red box, and a hanging light fixture.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

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

3. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 436

AED 487 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

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

4. Berkshire Mountain Lodge

19.5 km from Skyline Trail

marilyn

AED 315

AED 434 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A lakeside dock with kayaks and a covered boat ramp.

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

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

19.2 km from Skyline Trail

Bob

AED 425

AED 474 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

19.3 km from Skyline Trail

Sheldon

AED 378

AED 423 total

includes taxes & fees

2 Nov - 3 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 modern restaurant with wooden flooring, bar area, and seating arrangements.

7. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Tracy

AED 461

AED 515 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.

8. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

AED 422

AED 471 total

includes taxes & fees

4 Nov - 5 Nov

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

AED 470

AED 525 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 reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

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.

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

AED 555

AED 620 total

includes taxes & fees

1 Nov - 2 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.

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.

A cozy library with bookshelves, a fireplace, and comfortable seating.

11. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

AED 484

AED 540 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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

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

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

12. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Mark

AED 290

AED 324 total

includes taxes & fees

6 Oct - 7 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 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.

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

AED 962

AED 1,074 total

includes taxes & fees

4 Nov - 5 Nov

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

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.

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

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

AED 309

AED 345 total

includes taxes & fees

6 Oct - 7 Oct

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

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

15. FairBridge Inn Express

18 km from Skyline Trail

William

AED 228

AED 255 total

includes taxes & fees

6 Oct - 7 Oct

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

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

AED 294

AED 329 total

includes taxes & fees

6 Oct - 7 Oct

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Top Skyline Trail Hotel Reviews

Berkshires Untold

8/10 Good

"Fantastic location, and friendly staff. The rooms were comfortable."

The Central Downtown Inn & Suites

8/10 Good

"The staff were helpful and the room was clean. Overall the experience was good"

Hotel On North

8/10 Good

"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."

Quality Inn Lee - Lenox South

10/10 Excellent

"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"

Element by Marriott Lenox Berkshires

10/10 Excellent

"Stayed end of Sept 2026 for 3 nights. Booked the standard room with 2 queen beds. Very clean, spacious, great amenities (microwave, mini fridge, dishes, utensils and sink), spacious closet with drawers and closet rod & hangers. EV charging in parking lot. Breakfast included. Convenient location. Friendly & helpful staff. Would stay there again."

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"I was only there to sleep for a few hours"

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 AED 255

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

2. Quality Inn Lee - Lenox South

3. Berkshire Lake Lodge

4. Berkshire Mountain Lodge

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

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

7. Courtyard by Marriott Lenox Berkshires

8. Hampton Inn & Suites Berkshires-Lenox

9. Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

11. Berkshires Untold

12. Howard Johnson by Wyndham Lenox

13. Chambery Inn

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Top Skyline Trail Hotel Reviews

Berkshires Untold

The Central Downtown Inn & Suites

Hotel On North

Quality Inn Lee - Lenox South

Element by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

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