The 10 Best Hotels Near Skyline Trail, Middlefield from CA $100

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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 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.

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

Basil

CA $134

CA $150 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

2. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Lucinda

CA $130

CA $145 total

includes taxes & fees

Nov 15 - Nov 16

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

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

19.3 km from Skyline Trail

Ginger

CA $139

CA $155 total

includes taxes & fees

Nov 22 - Nov 23

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

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

A lakeside dock with kayaks and a covered boat ramp.

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

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

19.2 km from Skyline Trail

Gustavo

CA $161

CA $180 total

includes taxes & fees

Nov 15 - Nov 16

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.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

5. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Vandhana

CA $176

CA $197 total

includes taxes & fees

Nov 8 - Nov 9

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

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A wooden cabinet with a coffee maker and a white container.

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

6. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Thomas

CA $154

CA $172 total

includes taxes & fees

Oct 30 - Oct 31

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.

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

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

7. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

CA $180

CA $201 total

includes taxes & fees

Nov 8 - Nov 9

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 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".

8. Berkshires Untold

19.8 km from Skyline Trail

Madhavi R

CA $183

CA $204 total

includes taxes & fees

Nov 1 - Nov 2

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".

9. Berkshire Mountain Lodge

19.5 km from Skyline Trail

ulla

CA $120

CA $165 total

includes taxes & fees

Nov 10 - Nov 11

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 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.

10. Berkshire Lake Lodge

13 km from Skyline Trail

mike

CA $170

CA $190 total

includes taxes & fees

Nov 12 - Nov 13

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.

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

An outdoor seating area with Adirondack chairs and a fire feature.

11. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Francis

CA $190

CA $212 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

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

Alexandra

CA $315

CA $352 total

includes taxes & fees

Nov 17 - Nov 18

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures 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, 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.

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Aleksandr

CA $111

CA $124 total

includes taxes & fees

Oct 25 - Oct 26

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

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

A hotel room with two beds, a chair, and a bedside table with a phone.

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

14. Sunset Inn

18.6 km from Skyline Trail

Lauren

CA $114

CA $127 total

includes taxes & fees

Nov 4 - Nov 5

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

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

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

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

Richard

CA $90

CA $100 total

includes taxes & fees

Oct 27 - Oct 28

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 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.

16. Pilgrim Inn

18.5 km from Skyline Trail

james

CA $113

CA $126 total

includes taxes & fees

Oct 28 - Oct 29

View all properties

Compare popular hotels close to Skyline Trail

Property	Star rating	Guest rating
The Yankee Inn	9.2 Wonderful 1,012 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,001 reviews	View
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG	9.2 Wonderful 244 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,007 reviews	View
Courtyard by Marriott Lenox Berkshires	9.2 Wonderful 679 reviews	View

Top Skyline Trail Hotel Reviews

Quality Inn Lee - Lenox South

8/10 Good

"Ok"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Check in & out were easy. Mint restaurant was GREAT. View from the balcony overlooking the lake was super. Same weekend for the last four years & we will be back."

The Yankee Inn

8/10 Good

"Efficient & comfortable. Very good value."

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."

The Central Downtown Inn & Suites

8/10 Good

"I liked the location and the restaurant was good"

Element by Marriott Lenox Berkshires

10/10 Excellent

"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"

Hilton Garden Inn Lenox Pittsfield

8/10 Good

"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."

Howard Johnson by Wyndham Lenox

8/10 Good

"We enjoyed our stay, staff was very friendly."

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.

See properties

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.

See properties

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.

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 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.

Find hotels near Skyline Trail, Middlefield from CA $100

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Treat yourself

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Check prices for these dates

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Star rating

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Our top choices for Skyline Trail hotels

1. The Yankee Inn

2. Quality Inn Lee - Lenox South

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

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

5. Courtyard by Marriott Lenox Berkshires

6. Hampton Inn & Suites Berkshires-Lenox

7. Hilton Garden Inn Lenox Pittsfield

8. Berkshires Untold

9. Berkshire Mountain Lodge

10. Berkshire Lake Lodge

11. Element by Marriott Lenox Berkshires

12. Chambery Inn

13. Howard Johnson by Wyndham Lenox

14. Sunset Inn

15. FairBridge Inn Express

16. Pilgrim Inn

Compare popular hotels close to Skyline Trail

Top Skyline Trail Hotel Reviews

Quality Inn Lee - Lenox South

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Hotel On North

Hampton Inn & Suites Berkshires-Lenox

The Central Downtown Inn & Suites

Element by Marriott Lenox Berkshires

Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

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

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