The Best Hotels Closest to Skyline Trail in Middlefield for 2026

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Our top choices for Skyline Trail hotels

2 full Extra Long Beds | Desk, laptop workspace, WiFi (free)

1. Berkshire Lake Lodge

13 km from Skyline Trail

mike

AED 551

AED 616 total

includes taxes & fees

20 Sep - 21 Sep

Deluxe Suite | Iron/ironing board, WiFi (free), individually decorated

Fire Spa Suite | Iron/ironing board, WiFi (free), individually decorated

2. Chambery Inn

18.9 km from Skyline Trail

Alexandra

AED 942

AED 1,052 total

includes taxes & fees

27 Sep - 28 Sep

3. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Kirsty

AED 621

AED 693 total

includes taxes & fees

18 Oct - 19 Oct

Family House | Private kitchen | Coffee/tea maker, fridge, microwave

Standard Double Room, 1 Queen Bed, Non Smoking | Desk, WiFi (free), individually furnished, bed sheets

4. Becket Motel

11.3 km from Skyline Trail

Paul

AED 363

AED 528 total

includes taxes & fees

22 Sep - 23 Sep

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

19.3 km from Skyline Trail

Steve

AED 419

AED 468 total

includes taxes & fees

19 Oct - 20 Oct

6. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

James

AED 537

AED 600 total

includes taxes & fees

27 Sep - 28 Sep

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

Superior Room, 1 King Bed, Jetted Tub | Desk, laptop workspace, iron/ironing board, WiFi (free)

42-inch flat-screen TV with cable channels, TV

7. The Yankee Inn

19.6 km from Skyline Trail

Robert

AED 426

AED 476 total

includes taxes & fees

22 Sep - 23 Sep

8. Courtyard by Marriott Lenox Berkshires

19.9 km from Skyline Trail

Tracy

AED 731

AED 816 total

includes taxes & fees

20 Sep - 21 Sep

9. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Nancy

AED 464

AED 518 total

includes taxes & fees

28 Sep - 29 Sep

Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs (surcharge), rollaway beds (surcharge)

10. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Christine

AED 403

AED 450 total

includes taxes & fees

19 Oct - 20 Oct

11. Berkshires Untold

19.8 km from Skyline Trail

Drue

AED 514

AED 574 total

includes taxes & fees

28 Sep - 29 Sep

Basic Double Room | Blackout drapes, iron/ironing board (on request), WiFi (free)

12. Sunset Inn

18.6 km from Skyline Trail

Lauren

AED 306

AED 342 total

includes taxes & fees

5 Oct - 6 Oct

In-room safe, desk, laptop workspace, iron/ironing board

13. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

COLLEEN

AED 290

AED 324 total

includes taxes & fees

20 Sep - 21 Sep

Desk, laptop workspace, blackout drapes, soundproofing

14. Pilgrim Inn

18.5 km from Skyline Trail

"We got there and had to call the number, no one was at the desk. They called me back and said they notified Expedia they canceled all reservations, I did not receive any communication from Expedia. Do NOT book this hotel, it should not be on Expedia listing. I went to Tanglewood to see Carrie Underwood there was no other place that was in Expedia listings that were reasonable price. I drove home after the concert. A long night."

Anne

AED 294

AED 329 total

includes taxes & fees

1 Oct - 2 Oct

Desk, iron/ironing board, WiFi (free), bed sheets

Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, WiFi (free), bed sheets

15. FairBridge Inn Express

18 km from Skyline Trail

Horace

AED 228

AED 255 total

includes taxes & fees

20 Sep - 21 Sep

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Top Skyline Trail Hotel Reviews

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

10/10 Excellent

"Enjoyed the jacuzzi, the comfortable, spacious room, and staff was awesome!"

Quality Inn Lee - Lenox South

10/10 Excellent

"Great location for a trip to Tanglewood! Clean room, decent bedding, free breakfast, workout room, close to good restaurants. Would stay again"

Hotel On North

8/10 Good

"Our extended stay suite was spacious, comfortable and clean. The staff were kind and helpful. Overall our stay was very pleasant! John V."

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Clean and comfy"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Nice place, would stay again"

The Central Downtown Inn & Suites

8/10 Good

"It was priced well. The central location was convenient. The space inside was much larger than usual. There was a bedroom, living room and dining room combo with a full kitchen. It appears that it was an apartment at one time."

Element by Marriott Lenox Berkshires

10/10 Excellent

"Stay was nice"

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 during your trip to Chester. Wander the lakeside and forest 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 cozy coffeehouses. You'll find 14 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 14 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.

Where can I learn more about changing or cancelling my trip in the area near Skyline Trail?

For more information about picking new dates or cancelling your stay near Skyline Trail, head over to our customer service page.

Find hotels near Skyline Trail, Middlefield from AED 255

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Our top choices for Skyline Trail hotels

1. Berkshire Lake Lodge

2. Chambery Inn

3. Element by Marriott Lenox Berkshires

4. Becket Motel

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

6. Hilton Garden Inn Lenox Pittsfield

7. The Yankee Inn

8. Courtyard by Marriott Lenox Berkshires

9. Hampton Inn & Suites Berkshires-Lenox

10. Quality Inn Lee - Lenox South

11. Berkshires Untold

12. Sunset Inn

13. Howard Johnson by Wyndham Lenox

14. Pilgrim Inn

15. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

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

Quality Inn Lee - Lenox South

Hotel On North

Courtyard by Marriott Lenox Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Central Downtown Inn & Suites

Element 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