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 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.

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.

1. The Yankee Inn

19.6 km from Skyline Trail

Basil

₹10,254

₹11,454 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 hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

2. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

₹8,963

₹10,011 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 lakeside lodge with a dock, fishing rods, and outdoor seating.

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

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

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

19.2 km from Skyline Trail

Bob

₹11,429

₹12,766 total

includes taxes & fees

10 Nov - 11 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.

4. Berkshire Lake Lodge

13 km from Skyline Trail

mike

₹12,615

₹14,091 total

includes taxes & fees

2 Nov - 3 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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

5. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Tracy

₹12,151

₹13,573 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel patio with outdoor seating and a fire pit.

6. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

₹12,370

₹13,818 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.

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

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

7. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

₹12,594

₹14,067 total

includes taxes & fees

1 Nov - 2 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 conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

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

8. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

₹11,018

₹12,307 total

includes taxes & fees

7 Nov - 8 Nov

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

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

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.

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

19.3 km from Skyline Trail

Ginger

₹9,577

₹10,697 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.

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

₹13,833

₹15,452 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

11. Berkshire Mountain Lodge

19.5 km from Skyline Trail

marilyn

₹8,292

₹11,424 total

includes taxes & fees

9 Nov - 10 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

₹7,642

₹8,536 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 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.

13. Chambery Inn

18.9 km from Skyline Trail

Alexandra

₹23,245

₹25,964 total

includes taxes & fees

11 Nov - 12 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 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.

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

₹8,619

₹9,628 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 dining area with wooden tables and chairs, a television, and a door with a sign.

15. FairBridge Inn Express

18 km from Skyline Trail

William

₹6,007

₹6,710 total

includes taxes & fees

12 Oct - 13 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 modern bathroom with a marble countertop, a round mirror, a black coffee machine, a microwave, and a black refrigerator.

16. Pilgrim Inn

18.5 km from Skyline Trail

james

₹7,748

₹8,656 total

includes taxes & fees

24 Oct - 25 Oct

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Top Skyline Trail Hotel Reviews

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 Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

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!"

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 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.

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

4. Berkshire Lake Lodge

5. Courtyard by Marriott Lenox Berkshires

6. Hilton Garden Inn Lenox Pittsfield

7. Berkshires Untold

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. Howard Johnson by Wyndham Lenox

13. Chambery Inn

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Top Skyline Trail Hotel Reviews

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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

Element by Marriott Lenox Berkshires

Quality Inn Lee - Lenox South

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