Holiday rentals near Skyline Trail
We found 743 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Skyline Trail that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, including Wi-Fi and parking. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Skyline Trail
Showing deals for:13 Feb - 20 Feb
Image gallery for Hill Ross Guest Suite on Historic Homestead

10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Hill Ross Guest Suite on Historic Homestead
Florence, MA
12% off
Price is AU$5,753
for 7 nights, 1 home
AU$822 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Skyline Trail

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
10 out of 10
exceptional
(241 reviews)
Top rated rentals - Skyline Trail

Lakeside in the Berkshires
10 out of 10
exceptional
(64 reviews)
This home was perfect for our family over the thanksgiving weekend. It has three levels and that provided privacy while the living area was open. Very clean, comfortable beds, a well stocked kitchen and good location for exploring Stockbridge and Lenox. Hiking trails and canoeing made it great for activities. The owner communicated answering questions promptly and left simple instructions for the home. Loved staying here.
Donna M.
Stayed Nov 2024
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value




























