The Best Hotels Closest to Skyline Trail in Middlefield - 2026 Updated Prices

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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 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 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

William

฿3,557

฿3,973 total

includes taxes & fees

1 Nov - 2 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.

2. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

฿3,680

฿4,110 total

includes taxes & fees

25 Oct - 26 Oct

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.

3. Berkshire Mountain Lodge

19.5 km from Skyline Trail

marilyn

฿2,877

฿3,963 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

4. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Tracy

฿4,215

฿4,709 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 modern cafe with a counter, seating area, and large windows.

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

19.3 km from Skyline Trail

Sheldon

฿3,457

฿3,861 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

฿4,281

฿4,782 total

includes taxes & fees

6 Oct - 7 Oct

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 lodge with a large building and a dock by a lake, surrounded by forest.

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

19.2 km from Skyline Trail

Bob

฿3,879

฿4,333 total

includes taxes & fees

1 Nov - 2 Nov

A modern bathroom with a wooden vanity, a toilet, and two framed pictures on the wall.

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.

8. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

฿3,853

฿4,303 total

includes taxes & fees

4 Nov - 5 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.

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

฿4,292

฿4,794 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

฿5,067

฿5,660 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 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 sofa, a coffee table, and a large window with a view of trees.

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

11. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

฿4,418

฿4,935 total

includes taxes & fees

1 Nov - 2 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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

12. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Mark

฿2,651

฿2,961 total

includes taxes & fees

6 Oct - 7 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 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.

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

฿9,061

฿10,121 total

includes taxes & fees

4 Nov - 5 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

฿2,824

฿3,154 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 desk, computer, TV, and a chair.

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

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

15. FairBridge Inn Express

18 km from Skyline Trail

William

฿2,084

฿2,328 total

includes taxes & fees

6 Oct - 7 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 well-lit dining area with a round table and chairs, a potted plant, and a view through large windows.

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

฿2,688

฿3,003 total

includes taxes & fees

6 Oct - 7 Oct

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Compare popular hotels close to Skyline Trail

Property	Property class	Guest rating
The Yankee Inn	9.2 Wonderful 1,007 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,004 reviews	View
Berkshire Mountain Lodge	9.0 Wonderful 1,173 reviews	View
Courtyard by Marriott Lenox Berkshires	9.2 Wonderful 662 reviews	View
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG	9.2 Wonderful 227 reviews	View

Top Skyline Trail Hotel Reviews

Berkshires Untold

8/10 Good

"Fantastic location, and friendly staff. The rooms were comfortable."

The Central Downtown Inn & Suites

8/10 Good

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

Hotel On North

8/10 Good

"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."

Quality Inn Lee - Lenox South

10/10 Excellent

"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"

Element by Marriott Lenox Berkshires

10/10 Excellent

"Stayed end of Sept 2026 for 3 nights. Booked the standard room with 2 queen beds. Very clean, spacious, great amenities (microwave, mini fridge, dishes, utensils and sink), spacious closet with drawers and closet rod & hangers. EV charging in parking lot. Breakfast included. Convenient location. Friendly & helpful staff. Would stay there again."

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"I was only there to sleep for a few hours"

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 on your trip to Chester. Wander the lakeside and forests 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 cosy cafes. You'll find 15 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay near Skyline Trail?

Berkshire Mountain Lodge is one of the top choices for your stay based on our traveller 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 options in the area include FairBridge Inn Express and The Yankee Inn.

How many hotels are there close to Skyline Trail?

Expedia has 15 hotels and other accommodation options 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! The majority of hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to view top deals close to Skyline Trail.

Search Hotels Near Skyline Trail, Middlefield

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

2. Quality Inn Lee - Lenox South

3. Berkshire Mountain Lodge

4. Courtyard by Marriott Lenox Berkshires

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

6. Berkshire Lake Lodge

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

8. Hampton Inn & Suites Berkshires-Lenox

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. FairBridge Inn Express

16. Pilgrim Inn

Compare popular hotels close to Skyline Trail

Top Skyline Trail Hotel Reviews

Berkshires Untold

The Central Downtown Inn & Suites

Hotel On North

Quality Inn Lee - Lenox South

Element by Marriott Lenox Berkshires

Courtyard by Marriott Lenox 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