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Our top choices for Skyline Trail hotels

1. The Yankee Inn

The Yankee Inn
19.6 km from Skyline Trail
United States
Karen
CA $145
CA $162 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn

2. Berkshire Lake Lodge

Berkshire Lake Lodge
13 km from Skyline Trail
United States
mike
CA $199
CA $223 total
includes taxes & fees
Sep 23 - Sep 24
Berkshire Lake Lodge

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
19.2 km from Skyline Trail
United States
Susan
CA $173
CA $194 total
includes taxes & fees
Sep 21 - Sep 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
19.3 km from Skyline Trail
United States
Steve
CA $176
CA $197 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

5. Berkshires Untold

Berkshires Untold
19.8 km from Skyline Trail
United States
Drue
CA $183
CA $204 total
includes taxes & fees
Sep 16 - Sep 17
Berkshires Untold

6. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
19.5 km from Skyline Trail
United States
Nancy
CA $185
CA $207 total
includes taxes & fees
Sep 23 - Sep 24
Hampton Inn & Suites Berkshires-Lenox

7. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
18.6 km from Skyline Trail
United States
Christine
CA $149
CA $166 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Lee - Lenox South

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
19.5 km from Skyline Trail
United States
Robert
CA $110
CA $154 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge

9. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
19.4 km from Skyline Trail
United States
James
CA $203
CA $227 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
19.8 km from Skyline Trail
United States
Kirsty
CA $247
CA $276 total
includes taxes & fees
Sep 20 - Sep 21
Element by Marriott Lenox Berkshires

11. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
19.9 km from Skyline Trail
United States
Tracy
CA $272
CA $304 total
includes taxes & fees
Sep 20 - Sep 21
Courtyard by Marriott Lenox Berkshires

12. Chambery Inn

Chambery Inn
18.9 km from Skyline Trail
United States
Alexandra
CA $360
CA $402 total
includes taxes & fees
Sep 21 - Sep 22
Chambery Inn

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
19.5 km from Skyline Trail
United States
COLLEEN
CA $110
CA $122 total
includes taxes & fees
Sep 15 - Sep 16
Howard Johnson by Wyndham Lenox

14. Sunset Inn

Sunset Inn
18.6 km from Skyline Trail
United States
Lauren
CA $117
CA $130 total
includes taxes & fees
Oct 5 - Oct 6
Sunset Inn

15. Becket Motel

Becket Motel
11.3 km from Skyline Trail
United States
Paul
CA $133
CA $195 total
includes taxes & fees
Sep 27 - Sep 28
Becket Motel

16. FairBridge Inn Express

FairBridge Inn Express
18 km from Skyline Trail
United States
Horace
CA $86
CA $96 total
includes taxes & fees
Sep 15 - Sep 16
FairBridge Inn Express
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Top Skyline Trail Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The hotel is a perfect place to stay when attending a concert at Tanglewood. Its location is very convenient and our room was clean and comfortable. The on site restaurant (Mint) is lively and serves delicious Indian food."
William 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 8 hours ago
The Yankee Inn
Berkshires Untold

Berkshires Untold

8/10 Good
"Location was great! We loved the new addition in the front, where the reception area was, as well as restaurant and bar area, and library. Also liked the fire pits and outdoor seating. Rooms themselves were very basic and motel-like, and rather dark, but they did have nice bath products (shampoo, conditioner and body lotion). We didn’t realize there was also a room darkening shade on the front window, so the first night we just closed the curtain, which was see-thru! Staff was pleasant, and coffee was ready bright and early."
Barbara A 2-night trip
Posted 8 hours ago
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"All the staff I encountered were helpful and friendly. Room was modern and spacious. The free breakfast was very good. I loved the pool and the hot tub! I had an excellent 2-night stay!"
Victoria 2-night trip
Posted 1 day ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Therooms were loud on the lower level."
Sheila 1-night trip
Posted 1 day ago
Quality Inn Lee - Lenox South
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Great stay. Clean hotel with immaculate amenities. My grandson enjoyed the Pool. The washer and dryer were helpful. The staff at the front desk were so sweet. And the breakfast at the cafe was great. Nice views and location. Brewery! restaurants across the street. This lace was very comfortable and clean. Highly recommend."
Valerie 1-night trip
Posted 3 days ago
Courtyard by Marriott Lenox Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Michael 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Central Downtown Inn & Suites

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."
Phillip 1-night trip
Posted 6 days ago
The Central Downtown Inn & Suites
Hotel On North

Hotel On North

10/10 Excellent
"Best place in town"
Mary Ellen 2-night trip
Posted 6 days ago
Hotel On North

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.
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 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.

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