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

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

AED 389

AED 435 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.

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

19.3 km from Skyline Trail

Ginger

AED 364

AED 406 total

includes taxes & fees

12 Nov - 13 Nov

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.

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.

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

19.2 km from Skyline Trail

Gustavo

AED 418

AED 467 total

includes taxes & fees

15 Nov - 16 Nov

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.

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

4. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

AED 340

AED 380 total

includes taxes & fees

4 Nov - 5 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 large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

5. 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.

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

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.

6. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

AED 478

AED 534 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

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

8. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 469

AED 523 total

includes taxes & fees

2 Nov - 3 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 modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

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 470

AED 525 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.

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

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

10. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Kathleen

AED 315

AED 434 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

11. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

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 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.

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

18 Oct - 19 Oct

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

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.

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

25 Oct - 26 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 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.

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

AED 327

AED 366 total

includes taxes & fees

26 Oct - 27 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.

15. FairBridge Inn Express

18 km from Skyline Trail

William

AED 243

AED 271 total

includes taxes & fees

29 Oct - 30 Oct

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 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

View all properties

Compare popular hotels close to Skyline Trail

Property	Property class	Guest rating
The Yankee Inn	9.2 Wonderful 1,001 reviews	View
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG	9.4 Exceptional 238 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,001 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,000 reviews	View
Hampton Inn & Suites Berkshires-Lenox	9.0 Wonderful 1,001 reviews	View

Top Skyline Trail Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Clean room - great linens- very welcoming- great choices for breakfast- superior coffee, hot chocolate, latte machine. Great value for the price we paid."

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

Berkshire Mountain Lodge

10/10 Excellent

"The bath tub and the wash basin had some water clogging"

The Central Downtown Inn & Suites

10/10 Excellent

"Consistently, a clean, quiet, convenient location and comfortable stay."

Howard Johnson by Wyndham Lenox

8/10 Good

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

Hotel On North

10/10 Excellent

"The hotel is charming in the heart of Pittsfield. The rooms were large and clean. It’s a great boutique hotel with 35 rooms. There is a restaurant attached to the hotel that had great food and drinks! Will definitely be back."

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Sitting around the fire pit after a long day of leaf peeping was glorious..."

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.

See properties

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 271

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Treat yourself

Be picky

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

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

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

4. Quality Inn Lee - Lenox South

5. Hampton Inn & Suites Berkshires-Lenox

6. Berkshires Untold

7. Courtyard by Marriott Lenox Berkshires

8. Berkshire Lake Lodge

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

Compare popular hotels close to Skyline Trail

Top Skyline Trail Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

FairBridge Inn Express

Berkshire Mountain Lodge

The Central Downtown Inn & Suites

Howard Johnson by Wyndham Lenox

Hotel On North

Courtyard by Marriott Lenox Berkshires

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