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

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Our top choices for Skyline Trail hotels

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

1. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Lucinda

2.397.133 ₫

2.677.598 ₫ total

includes taxes & fees

5 Nov - 6 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 modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

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

19.3 km from Skyline Trail

Ginger

2.561.427 ₫

2.861.114 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

3. The Yankee Inn

19.6 km from Skyline Trail

Basil

2.742.538 ₫

3.063.414 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A room with two beds, a round mirror, a red box, and a hanging light fixture.

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

4. Berkshire Lake Lodge

13 km from Skyline Trail

mike

3.667.498 ₫

4.096.596 ₫ 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, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

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

2.836.974 ₫

3.168.900 ₫ total

includes taxes & fees

2 Nov - 3 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.

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

19.2 km from Skyline Trail

Gustavo

2.946.935 ₫

3.291.727 ₫ total

includes taxes & fees

15 Nov - 16 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.

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.

7. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

3.249.908 ₫

3.630.147 ₫ 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 spacious lobby with a fireplace, seating area, and a bar.

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

8. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Joel

2.238.778 ₫

3.078.718 ₫ total

includes taxes & fees

15 Nov - 16 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 large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

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

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

3.308.639 ₫

3.695.699 ₫ 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.

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.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

10. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

3.492.855 ₫

3.901.520 ₫ 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, 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.

11. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

2.043.967 ₫

2.283.111 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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.

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

12. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

3.368.385 ₫

3.762.486 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

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.

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

13. Sunset Inn

18.6 km from Skyline Trail

Lauren

2.095.713 ₫

2.340.912 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 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.

14. Chambery Inn

18.9 km from Skyline Trail

Alexandra

6.985.451 ₫

7.802.779 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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.

15. Pilgrim Inn

18.5 km from Skyline Trail

james

2.072.427 ₫

2.314.900 ₫ 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 desk, computer, TV, and a chair.

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

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

16. FairBridge Inn Express

18 km from Skyline Trail

Richard

1.839.570 ₫

2.054.800 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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Top Skyline Trail Hotel Reviews

The Yankee Inn

10/10 Excellent

"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."

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!"

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."

Quality Inn Lee - Lenox South

8/10 Good

"Had a comfortable stay."

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

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. Quality Inn Lee - Lenox South

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

3. The Yankee Inn

4. Berkshire Lake Lodge

5. Hampton Inn & Suites Berkshires-Lenox

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

7. Courtyard by Marriott Lenox Berkshires

8. Berkshire Mountain Lodge

9. Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

11. Howard Johnson by Wyndham Lenox

12. Berkshires Untold

13. Sunset Inn

14. Chambery Inn

15. Pilgrim Inn

16. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

The Yankee Inn

FairBridge Inn Express

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

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