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

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.

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

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

SAR 334

SAR 373 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

19.2 km from Skyline Trail

Gustavo

SAR 427

SAR 477 total

includes taxes & fees

15 Nov - 16 Nov

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

A hotel room with a bed, a desk, a chair, and a carpeted floor.

3. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

SAR 411

SAR 460 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

4. Berkshire Lake Lodge

13 km from Skyline Trail

mike

SAR 479

SAR 535 total

includes taxes & fees

2 Nov - 3 Nov

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.

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

5. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Lucinda

SAR 348

SAR 388 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

Ginger

SAR 357

SAR 398 total

includes taxes & fees

17 Nov - 18 Nov

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

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.

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

7. 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 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".

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

8. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Joel

SAR 325

SAR 447 total

includes taxes & fees

10 Nov - 11 Nov

A hotel patio with outdoor seating and a fire pit.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

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 480

SAR 536 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.

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.

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

SAR 507

SAR 566 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

11. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

SAR 489

SAR 546 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.

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.

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

12. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

SAR 296

SAR 331 total

includes taxes & fees

18 Oct - 19 Oct

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

SAR 871

SAR 973 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 standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

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.

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 two beds, a nightstand, a lamp, and a patterned floor.

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.

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

15. Pilgrim Inn

18.5 km from Skyline Trail

james

SAR 301

SAR 336 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

16. FairBridge Inn Express

18 km from Skyline Trail

Richard

SAR 240

SAR 268 total

includes taxes & fees

8 Nov - 9 Nov

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Top Skyline Trail Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"We were able to get rental as a last minute deal for a villa here and we're very pleased with the property. The two rooms were very spacious each with its own bathroom, one with jacuuzi. Was quiet and you don't see or hear neighbor next to you. The rooms were quite roomy. All amenities in kitchen and nice livingroom/dining area. Nice outdoor seating with table and nice view of mountains. Only issue encountered was figuring out how the showers worked, figured it out by pulling down a round lever on bottom of faucet. Very clean and spacious, nice experience."

Berkshires Untold

10/10 Excellent

"Great room and great bar. It takes time but is worth it"

Courtyard by Marriott Lenox Berkshires

8/10 Good

"Property was clean and in excellent shape overall. Pros: Food at the Bistro was excellent quality, and large portions. Room was clean and comfortable, slept well while staying there. Onsite laundry was a very helpful option and the washer and dryer, while expensive at $4.00 a load, were in excellent condition and did the job very well. Pool and hot tub were excellent. Cons: The light switches governing the various lights in the room were a little confusing at first. The free HBO had severe buffering issues, making watching anything on it tough. The controls for the automatic curtain open/shut were broken, making one start the open and shut manually. Overall, the Pros well outweighed the Cons."

The Whitlock

10/10 Excellent

"This property was the perfect location to enjoy downtown Lennox and very close to our friends’ son’s wedding at Tanglewood. I’d stay again!"

Quality Inn Lee - Lenox South

8/10 Good

"Pleasant stay, nice and clean conditions."

The Yankee Inn

10/10 Excellent

"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."

Howard Johnson by Wyndham Lenox

8/10 Good

"Clean, parking, room all good. Staff was very welcome and helpful."

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

10/10 Excellent

"New hotel with clean"

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."

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 268

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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. Hampton Inn & Suites Berkshires-Lenox

4. Berkshire Lake Lodge

5. Quality Inn Lee - Lenox South

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

7. Courtyard by Marriott Lenox Berkshires

8. Berkshire Mountain Lodge

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. Pilgrim Inn

16. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshires Untold

Courtyard by Marriott Lenox Berkshires

The Whitlock

Quality Inn Lee - Lenox South

The Yankee Inn

Howard Johnson by Wyndham Lenox

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

The Cornell Inn, Lenox & The 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