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

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Our top choices for Skyline Trail hotels

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

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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.

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

19.3 km from Skyline Trail

Ken

₹11,354

₹12,683 total

includes taxes & fees

24 Sept - 25 Sept

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 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.

2. Berkshire Lake Lodge

13 km from Skyline Trail

mike

₹13,199

₹14,743 total

includes taxes & fees

9 Sept - 10 Sept

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

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

3. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Nancy

₹11,817

₹13,200 total

includes taxes & fees

9 Sept - 10 Sept

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 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.

4. The Yankee Inn

19.6 km from Skyline Trail

Karen

₹14,503

₹16,199 total

includes taxes & fees

27 Sept - 28 Sept

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

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.

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

19.2 km from Skyline Trail

Rinat

₹12,165

₹13,588 total

includes taxes & fees

16 Sept - 17 Sept

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

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".

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

6. Berkshires Untold

19.8 km from Skyline Trail

Christine

₹13,526

₹15,109 total

includes taxes & fees

7 Sept - 8 Sept

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 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.

7. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Lawrence

₹16,983

₹18,970 total

includes taxes & fees

7 Sept - 8 Sept

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

A garden with wooden Adirondack chairs and a stone pathway.

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

Robert

₹9,026

₹12,213 total

includes taxes & fees

31 Aug - 1 Sept

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

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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.

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

₹14,045

₹15,688 total

includes taxes & fees

13 Sept - 14 Sept

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.

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

10. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

₹10,462

₹11,686 total

includes taxes & fees

16 Sept - 17 Sept

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

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

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.

11. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Laura

₹16,950

₹18,933 total

includes taxes & fees

7 Sept - 8 Sept

A two-story building with a sign reading "Chambéry Inn".

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.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

12. Chambery Inn

18.9 km from Skyline Trail

Richard

₹25,760

₹28,775 total

includes taxes & fees

27 Sept - 28 Sept

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

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Sheila

₹7,538

₹8,420 total

includes taxes & fees

31 Aug - 1 Sept

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

Kevin

₹8,862

₹9,899 total

includes taxes & fees

1 Sept - 2 Sept

A building with a flat roof, multiple windows, and a satellite dish.

An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.

A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.

A dining area with a round table set for four, surrounded by dark chairs. A white door is visible in the background, leading to a kitchen area with white appliances.

15. Becket Motel

11.3 km from Skyline Trail

Paul

₹9,417

₹13,716 total

includes taxes & fees

24 Sept - 25 Sept

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.

16. FairBridge Inn Express

18 km from Skyline Trail

ERICIA

₹5,688

₹6,354 total

includes taxes & fees

30 Aug - 31 Aug

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Top Skyline Trail Hotel Reviews

The Yankee Inn

10/10 Excellent

"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."

Hotel On North

10/10 Excellent

"No comment."

Berkshire Mountain Lodge

10/10 Excellent

"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"

Element by Marriott Lenox Berkshires

10/10 Excellent

"I loved the saline pool and the fire pits!!! Breakfast was great, too. The bed was comfy and the room was spacious. I couldn't have asked for a nicer place to stay."

Berkshire Inn

10/10 Excellent

"Easy spot for a Tanglewood event. Swam in the pool. Walked to Breakfast."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"We were there for one night and it worked out great. Nice breakfast!"

Quality Inn Lee - Lenox South

8/10 Good

"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."

The Central Downtown Inn & Suites

10/10 Excellent

"Clean room (suite). Property well maintained. Communication was done via text messages."

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

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 13 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay near Skyline Trail?

The Yankee Inn is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and an outdoor pool. You'll find it 12.2 mi (19.6 km) from Skyline Trail. Other good options in the area include FairBridge Inn Express and Berkshire Mountain Lodge.

How many hotels are there close to Skyline Trail?

Expedia has 13 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. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2. Berkshire Lake Lodge

3. Hampton Inn & Suites Berkshires-Lenox

4. The Yankee Inn

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

6. Berkshires Untold

7. Element by Marriott Lenox Berkshires

8. Berkshire Mountain Lodge

9. Hilton Garden Inn Lenox Pittsfield

10. Quality Inn Lee - Lenox South

11. Courtyard by Marriott Lenox Berkshires

12. Chambery Inn

13. Howard Johnson by Wyndham Lenox

14. Sunset Inn

15. Becket Motel

16. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

The Yankee Inn

Hotel On North

Berkshire Mountain Lodge

Element by Marriott Lenox Berkshires

Berkshire Inn

Hampton Inn & Suites Berkshires-Lenox

Quality Inn Lee - Lenox South

The Central Downtown Inn & Suites

FairBridge Inn Express

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