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

Basil

AED 389

AED 435 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

AED 340

AED 380 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 dining area with large windows, wooden furniture, and a view of a lake.

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

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

AED 421

AED 471 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 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.

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

4. 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.

5. 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 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.

6. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

AED 418

AED 467 total

includes taxes & fees

7 Nov - 8 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 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.

7. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 479

AED 535 total

includes taxes & fees

11 Nov - 12 Nov

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

A spacious living room with a large sofa, a coffee table, and a fireplace.

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

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

A garden with wooden Adirondack chairs and a stone pathway.

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

9. Berkshire Mountain Lodge

19.5 km from Skyline Trail

marilyn

AED 315

AED 434 total

includes taxes & fees

9 Nov - 10 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 snack bar with shelves of snacks and a refrigerated display.

A modern cafe with a counter, seating area, and large windows.

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

19.3 km from Skyline Trail

Ginger

AED 364

AED 406 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 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

Kirsty

AED 525

AED 587 total

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

A white bench with bright pink cushions, a small potted plant, and decorative wall art including a sun and a crescent moon.

A window view of a garden with rocks, bushes, and trees.

A red door with a wreath, number 5, and flower baskets on either side.

12. The Red Door B&B

18.6 km from Skyline Trail

Anonymous traveler

AED 645

AED 1,028 total

includes taxes & fees

26 Oct - 27 Oct

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, a sofa, a coffee station, and a TV mounted 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.

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Mark

AED 290

AED 324 total

includes taxes & fees

18 Oct - 19 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 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.

14. Chambery Inn

18.9 km from Skyline Trail

Alexandra

AED 942

AED 1,052 total

includes taxes & fees

12 Nov - 13 Nov

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 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.

15. 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 fitness center including a weight machine, an elliptical, and a treadmill.

A dining area with wooden tables and chairs, a television, and a door with a sign.

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

16. FairBridge Inn Express

18 km from Skyline Trail

William

AED 228

AED 255 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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.

17. Pilgrim Inn

18.5 km from Skyline Trail

james

AED 294

AED 329 total

includes taxes & fees

24 Oct - 25 Oct

View all properties

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 1,001 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,003 reviews	View
Berkshires Untold	9.0 Wonderful 1,035 reviews	View
Courtyard by Marriott Lenox Berkshires	9.2 Wonderful 664 reviews	View

Top Skyline Trail Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Comfortable and cozy suite, large living room/dining area, kitchen and large bedroom, will stay again"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"My daughter and I stayed at this Inn for a girls weekend and it was a perfect way to kick off our fall weekend. From great service to delicious breakfast everything was taken care of."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

Quality Inn Lee - Lenox South

10/10 Excellent

"Good breakfast. Great location"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Good, but no restaurant is open for Dinner."

FairBridge Inn Express

8/10 Good

"Room was clean . Overall property was average but expected for the price"

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."

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."

The Central Downtown Inn & Suites

8/10 Good

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

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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Treat yourself

Be picky

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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. Berkshires Untold

5. Courtyard by Marriott Lenox Berkshires

6. Hampton Inn & Suites Berkshires-Lenox

7. Berkshire Lake Lodge

8. Hilton Garden Inn Lenox Pittsfield

9. Berkshire Mountain Lodge

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

11. Element by Marriott Lenox Berkshires

12. The Red Door B&B

13. Howard Johnson by Wyndham Lenox

14. Chambery Inn

15. Sunset Inn

16. FairBridge Inn Express

17. Pilgrim Inn

Compare popular hotels close to Skyline Trail

Top Skyline Trail Hotel Reviews

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Quality Inn Lee - Lenox South

Courtyard by Marriott Lenox Berkshires

FairBridge Inn Express

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Central Downtown Inn & Suites

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