Top Hotels Near Skyline Trail in Middlefield

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Jul - 23 Jul
Tomorrow
23 Jul - 24 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Accommodation near Skyline Trail

Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is NZ$216
includes taxes & fees
27 July - 28 July
Becket Motel
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (751)
"Close to our target event a plus"
The price is NZ$133
includes taxes & fees
5 Aug - 6 Aug
FairBridge Inn Express
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is NZ$147
includes taxes & fees
5 Aug - 6 Aug
Pilgrim Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (640)
"We enjoyed the unique character and flavor of the hotel!"
The price is NZ$807
includes taxes & fees
25 July - 26 July
Berkshires Untold
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (524)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
The price is NZ$227
includes taxes & fees
23 July - 24 July
Berkshire Mountain Lodge
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Loved the Yankee Inn!"
The price is NZ$253
includes taxes & fees
31 July - 1 Aug
The Yankee, Trademark Collection by Wyndham
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NZ$354
includes taxes & fees
27 July - 28 July
Hilton Garden Inn Lenox Pittsfield
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Friendly staff, easy parking"
The price is NZ$253
includes taxes & fees
6 Aug - 7 Aug
Quality Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NZ$333
includes taxes & fees
27 July - 28 July
Holiday Inn Express & Suites Pittsfield - Berkshires
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NZ$397
includes taxes & fees
24 July - 25 July
Courtyard by Marriott Lenox Berkshires
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (764)
"Was great loved the jacuzzi tub "
The price is NZ$185
includes taxes & fees
23 July - 24 July
Howard Johnson by Wyndham Lenox
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (393)
"No frills but it was a great stay!"
The price is NZ$196
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (611)
"Convenient location for my trip"
The price is NZ$129
includes taxes & fees
23 July - 24 July
Wagon Wheel Inn
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.

Top Skyline Trail Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Clean, smells good, newer amenities. Totally improved since two years ago. "
Olga 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox

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 cosy cafes. You'll find 12 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay near Skyline Trail?

Berkshires Untold is one of the top choices for your stay based on our traveller data, and this lodge offers a restaurant and free parking. You'll find it 12.3 mi (19.8 km) from Skyline Trail. Other good options in the area include FairBridge Inn Express and Quality Inn.

How many hotels are there close to Skyline Trail?

Expedia has 12 hotels and other accommodation options 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! The majority of hotel bookings are fully refundable if you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to view top deals close to Skyline Trail.