The Best Hotels Closest to Skyline Trail in Middlefield for 2026

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Our top choices for Skyline Trail hotels

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

19.3 km from Skyline Trail

Courtney

NT$5,645 total

includes taxes & fees

Aug 23 - Aug 24

2. Berkshire Lake Lodge

13 km from Skyline Trail

Grzegorz

NT$6,846 total

includes taxes & fees

Aug 3 - Aug 4

3. Berkshire Mountain Lodge

19.5 km from Skyline Trail

Joseph

NT$5,078 total

includes taxes & fees

Aug 23 - Aug 24

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

4. The Yankee Inn

19.6 km from Skyline Trail

Michael

NT$6,810 total

includes taxes & fees

Aug 2 - Aug 3

5. Berkshires Untold

19.8 km from Skyline Trail

Debra

NT$6,157 total

includes taxes & fees

Aug 23 - Aug 24

6. Hampton Inn & Suites Berkshires-Lenox

19.5 km from Skyline Trail

Barry

NT$6,505 total

includes taxes & fees

Aug 23 - Aug 24

7. Quality Inn Lee - Lenox South

18.6 km from Skyline Trail

Michelle

NT$5,471 total

includes taxes & fees

Jul 27 - Jul 28

8. Element by Marriott Lenox Berkshires

19.8 km from Skyline Trail

Izabela

NT$7,961 total

includes taxes & fees

Aug 19 - Aug 20

9. Hilton Garden Inn Lenox Pittsfield

19.4 km from Skyline Trail

Adeline

NT$6,965 total

includes taxes & fees

Jul 26 - Jul 27

10. Chambery Inn

18.9 km from Skyline Trail

Joseph

NT$9,770 total

includes taxes & fees

Jul 27 - Jul 28

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

11. Howard Johnson by Wyndham Lenox

19.5 km from Skyline Trail

Luciane

NT$3,586 total

includes taxes & fees

Jul 26 - Jul 27

12. Sunset Inn

18.6 km from Skyline Trail

Kevin

NT$3,745 total

includes taxes & fees

Aug 10 - Aug 11

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

13. FairBridge Inn Express

18 km from Skyline Trail

DAVID

NT$2,247 total

includes taxes & fees

Aug 20 - Aug 21

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Top Skyline Trail Hotel Reviews

Berkshires Untold

8/10 Good

"The HVAC unit in our room was loud. We couldn't find a way to quiet it or adjust the thermostat so that it ran less often."

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

10/10 Excellent

"The Holiday Inn Express Pittsfield-Lenox is a new (opened 10/25) lower cost hotel in the heart of the Berkshires, close to Tanglewood, Shakespeare and Company, The Berkshire Stage and most of the art and culture opportunities offered by the Berkshires. It is clean, the complementary hot breakfast is better than most, and the staff courteous and helpful. I highly recommend it and we will definitely return."

Howard Johnson by Wyndham Lenox

8/10 Good

"I selected due to the room rate- much lower - maybe half of others in the area. I knew what to expect- basic but it exceeded my expectations. Now under Wyndham, Howard Johnsons meets a higher standard- newer furniture, TV, renovated baths etc. Due to the newer LG TV, still needed programming- but got through it. Looked like a nice outside pool that was being used. It was just fine for the amount saved. Breakfast minimal but that's ok too. WIFI was fine."

FairBridge Inn Express

8/10 Good

"Room was clean and in excellent condition - apparently they have totally renovated since earlier reviews that mentioned severe problems. The exterior could use some paint, but the room was perfectly clean and fairly spacious. All the little things, like good A/C, shower temp/pressure, a working mini-fridge, etc., were completely fine. Complaints: I couldn't get the WiFi to work. Also: it's not in the most scenic part of Pittsfield, but it's just minutes from the nicer areas, and a short walk to fast food or decent chain restaurants like Friendlys, Applebees, and Starbucks."

Hotels near other Skyline Trail attractions

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

What's the best hotel to stay near Skyline Trail?

The Yankee Inn is one of the top choices for your stay based on our traveler 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 choices in the area include FairBridge Inn Express and Berkshire Mountain Lodge.

How many hotels can I expect to find close to Skyline Trail?

Expedia has 12 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 NT$2,247

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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. Berkshire Mountain Lodge

4. The Yankee Inn

5. Berkshires Untold

6. Hampton Inn & Suites Berkshires-Lenox

7. Quality Inn Lee - Lenox South

8. Element by Marriott Lenox Berkshires

9. Hilton Garden Inn Lenox Pittsfield

10. Chambery Inn

11. Howard Johnson by Wyndham Lenox

12. Sunset Inn

13. FairBridge Inn Express

Top Skyline Trail Hotel Reviews

Berkshires Untold

Hotels near other Skyline Trail attractions

Glendale Falls

Frequently asked questions

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