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

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

Basil

SAR 398

SAR 445 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

2. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

SAR 348

SAR 389 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 dock with kayaks and a covered boat ramp.

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

19.2 km from Skyline Trail

Bob

SAR 444

SAR 496 total

includes taxes & fees

10 Nov - 11 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.

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.

4. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Tracy

SAR 472

SAR 527 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 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.

5. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

SAR 489

SAR 546 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

6. Berkshire Lake Lodge

13 km from Skyline Trail

mike

SAR 500

SAR 559 total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel patio with outdoor seating and a fire pit.

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.

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

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

8. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

SAR 428

SAR 478 total

includes taxes & fees

7 Nov - 8 Nov

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

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

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.

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

19.3 km from Skyline Trail

Ginger

SAR 372

SAR 415 total

includes taxes & fees

8 Nov - 9 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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

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

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

SAR 537

SAR 600 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A garden with wooden Adirondack chairs and a stone pathway.

11. Berkshire Mountain Lodge

19.5 km from Skyline Trail

marilyn

SAR 322

SAR 444 total

includes taxes & fees

9 Nov - 10 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 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.

12. Chambery Inn

18.9 km from Skyline Trail

Alexandra

SAR 913

SAR 1,019 total

includes taxes & fees

11 Nov - 12 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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

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

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Mark

SAR 297

SAR 331 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

SAR 335

SAR 374 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 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

SAR 210

SAR 234 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a nightstand, a lamp, and a patterned floor.

A modern bathroom with a marble countertop, a round mirror, a black coffee machine, a microwave, and a black refrigerator.

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

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

16. Pilgrim Inn

18.5 km from Skyline Trail

james

SAR 301

SAR 336 total

includes taxes & fees

24 Oct - 25 Oct

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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
Quality Inn Lee - Lenox South	8.6 Excellent 1,000 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,003 reviews	View
Courtyard by Marriott Lenox Berkshires	9.2 Wonderful 663 reviews	View
Berkshires Untold	9.0 Wonderful 1,034 reviews	View

Top Skyline Trail Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"The hotel is an older building but is clean and well maintained. The view of the lake was nice. Breakfast was just ok. Bed was very comfortable. Michelle was very helpful. My only disappointment was that the kayaks were not complimentary. It cost $30 an hour for each kayak."

Berkshire Mountain Lodge

8/10 Good

"T"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Property was clean, staff friendly and helpful. Room was clean, tv channels were plentiful. Starbucks in lobby was extra nice and convenient. Overall great experience."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

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

10/10 Excellent

"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"

Berkshires Untold

10/10 Excellent

"Great, we'll run hotel"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely room, comfortable bed and a nice breakfast."

Element by Marriott Lenox Berkshires

10/10 Excellent

"Very airy lobby. Good breakfast. Large rooms."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

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 234

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

2. Quality Inn Lee - Lenox South

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

4. Courtyard by Marriott Lenox Berkshires

5. Berkshires Untold

6. Berkshire Lake Lodge

7. Hilton Garden Inn Lenox Pittsfield

8. Hampton Inn & Suites Berkshires-Lenox

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

10. Element by Marriott Lenox Berkshires

11. Berkshire Mountain Lodge

12. Chambery Inn

13. Howard Johnson by Wyndham Lenox

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

Berkshire Mountain Lodge

Courtyard by Marriott Lenox Berkshires

Holiday Inn Club Vacations Oak 'n Spruce Resort

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

Berkshires Untold

The Cornell Inn, Lenox & The Berkshires

Element by Marriott Lenox Berkshires

Quality Inn Lee - Lenox South

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