Default HTG hotel image

Find hotels near Skyline Trail, Middlefield from CA $97

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Jul 24 - Jul 26
Next weekend
Jul 31 - Aug 2

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Skyline Trail hotels

Indoor pool

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
19.3 km from Skyline Trail
9.4 out of 10, Exceptional, (137 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is CA $238
CA $266 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

2. The Yankee Inn

The Yankee Inn
2.5 star property
19.6 km from Skyline Trail
9.2 out of 10, Wonderful, (1,008 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is CA $192
CA $214 total
includes taxes & fees
Jul 22 - Jul 23
The Yankee Inn
Lake view

3. Berkshire Lake Lodge

Berkshire Lake Lodge
13 km from Skyline Trail
9.6 out of 10, Exceptional, (7 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is CA $284
CA $317 total
includes taxes & fees
Jul 22 - Jul 23
Berkshire Lake Lodge
Lobby

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
19.5 km from Skyline Trail
9.0 out of 10, Wonderful, (1,015 reviews)
"Great location too"
United States
judith
The price is CA $187
CA $241 total
includes taxes & fees
Aug 19 - Aug 20
Berkshire Mountain Lodge
Lobby

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
18.6 km from Skyline Trail
8.4 out of 10, Very good, (1,000 reviews)
"Great place"
United States
Michelle
The price is CA $190
CA $212 total
includes taxes & fees
Aug 17 - Aug 18
Quality Inn Lee - Lenox South
Lobby lounge

6. Berkshires Untold

Berkshires Untold
3.5 star property
19.8 km from Skyline Trail
9.0 out of 10, Wonderful, (1,003 reviews)
"Nice place to stay."
United States
Debra
The price is CA $231
CA $258 total
includes taxes & fees
Jul 23 - Jul 24
Berkshires Untold
Lobby

7. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
19.8 km from Skyline Trail
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $321
CA $359 total
includes taxes & fees
Jul 27 - Jul 28
Element by Marriott Lenox Berkshires
Free daily buffet breakfast

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
19.5 km from Skyline Trail
9.2 out of 10, Wonderful, (1,003 reviews)
"Perfect place to stay if going to Tanglewood or Stockbridge."
United States
Barry
The price is CA $275
CA $307 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn & Suites Berkshires-Lenox
Front of property

9. Chambery Inn

Chambery Inn
3.0 star property
18.9 km from Skyline Trail
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is CA $379
CA $423 total
includes taxes & fees
Aug 19 - Aug 20
Chambery Inn
Property amenity

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
19.9 km from Skyline Trail
9.2 out of 10, Wonderful, (639 reviews)
"I usually stay here when I'm going to a concert at Tanglewood, it's comfortable, quiet, and convenient. The staff are really friendly. There's a Tesla EV charging station directly across Route 20 from the hotel."
United States
Michael
The price is CA $309
CA $345 total
includes taxes & fees
Jul 26 - Jul 27
Courtyard by Marriott Lenox Berkshires
Breakfast, lunch and dinner served

11. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
19.4 km from Skyline Trail
9.2 out of 10, Wonderful, (696 reviews)
"Five Star stay!"
United States
Adeline
The price is CA $286
CA $320 total
includes taxes & fees
Jul 22 - Jul 23
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool

12. Sunset Inn

Sunset Inn
2.0 star property
18.6 km from Skyline Trail
7.6 out of 10, Good, (425 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is CA $142
CA $159 total
includes taxes & fees
Aug 10 - Aug 11
Sunset Inn
In-room safe, desk, laptop workspace, iron/ironing board

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
19.5 km from Skyline Trail
7.6 out of 10, Good, (885 reviews)
"Great place"
United States
Luciane
The price is CA $137
CA $153 total
includes taxes & fees
Jul 22 - Jul 23
Howard Johnson by Wyndham Lenox
Front of property

14. Becket Motel

Becket Motel
2.5 star property
11.3 km from Skyline Trail
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is CA $148
CA $212 total
includes taxes & fees
Jul 26 - Jul 27
Becket Motel
Desk, iron/ironing board, WiFi (free), bed sheets

15. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
18 km from Skyline Trail
5.4 out of 10, (857 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is CA $87
CA $97 total
includes taxes & fees
Jul 27 - Jul 28
FairBridge Inn Express
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Skyline Trail Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."
MaryLou 3-night trip
Posted 5 hours ago
The Yankee Inn

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.
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 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 Berkshire Mountain Lodge and FairBridge Inn Express.
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.

Explore a world of travel with Expedia