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 fireplace, a desk, a television, and a poster of a lake scene.

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

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

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

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 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.

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

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

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

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

A lakeside cabin with a dock, surrounded by dense forest and a clear view of the lake.

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

4. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 440

AED 491 total

includes taxes & fees

2 Nov - 3 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 cafe with a counter, seating area, and large windows.

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

5. 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 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.

6. 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 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.

7. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

AED 403

AED 450 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.

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

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

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

8. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

AED 478

AED 534 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

AED 436

AED 487 total

includes taxes & fees

15 Nov - 16 Nov

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

A garden with wooden Adirondack chairs and a stone pathway.

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

10. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Michael

AED 315

AED 434 total

includes taxes & fees

22 Nov - 23 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.

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

11. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Francis

AED 496

AED 554 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 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.

12. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

AED 290

AED 324 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

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

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

AED 853

AED 953 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 swimming pool with a fenced area, lounge chairs, and a warning sign.

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

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

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

AED 298

AED 332 total

includes taxes & fees

1 Nov - 2 Nov

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 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

AED 248

AED 277 total

includes taxes & fees

8 Nov - 9 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 modern bathroom with a marble vanity, a round mirror, a flat-screen TV, a microwave, and an air conditioning unit.

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

16. Pilgrim Inn

18.5 km from Skyline Trail

james

AED 294

AED 329 total

includes taxes & fees

28 Oct - 29 Oct

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Top Skyline Trail Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every night. If you want an old school meet the other visitors experience, you could probably have it. There is laundry on every floor. I think the awesome prices we got were due to it not being ski season? once we go there and did some driving around we realized Bousquet mountain was right there. So probably a brilliant choice for a long family ski trip. There are a couple of really convenient grocery stores and restaurants right there - but most of the tourist attractions and pittsfield downtown are 10minute or so drive away. Beautiful lobby/property. Enjoyed the coffee machine in the library. Really great experience. We'd love to stay again."

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 Central Downtown Inn & Suites

8/10 Good

"The unit was ok a bit dated. Our upstairs neighbors were walking around all day and night which wouldn't be a problem but every step they took rattled the dishes in the cabinet, thank god for earplugs."

Hotel On North

10/10 Excellent

"Can't wait to go back!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"After having been away from The Black Swan Inn since the 1980’s, I was happy to see the hotel is being maintained and cared for. The lakeside views are beautiful (even though I had to pay an up charge to get this side upon check in). The room was large. My only wish regarding the bedding, is that the pillows weren’t so hard and stiff. Balconies need a little maintenance. A staff member, “Rocky”, was especially nice to be greeted by in the breakfast room on the morning we left. Thank you."

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"

Quality Inn Lee - Lenox South

10/10 Excellent

"A"

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 AED 277

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Treat yourself

Be picky

Check prices for these dates

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

6. Courtyard by Marriott Lenox Berkshires

7. Hampton Inn & Suites Berkshires-Lenox

8. Berkshires Untold

9. Hilton Garden Inn Lenox Pittsfield

10. Berkshire Mountain Lodge

11. Element by Marriott Lenox Berkshires

12. Howard Johnson by Wyndham Lenox

13. Chambery Inn

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Top Skyline Trail Hotel Reviews

Berkshire Mountain Lodge

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

The Central Downtown Inn & Suites

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

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

Quality Inn Lee - Lenox South

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