Holiday rentals near Skyline Trail
We found 755 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:14 Nov - 21 Nov
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
10 out of 10 rating
Exceptional
(20 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
14% off
Price is AU$2,408
AU$344 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Skyline Trail
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(56 reviews)
Top rated rentals - Skyline Trail
Lakeside in the Berkshires
10 out of 10
exceptional
(61 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