Holiday In The Hamptons - Vacation Rentals in Skyline Trail

Berkshire Lake access From US $298
         

10.0 (61 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
1840's Ship Captain's Farm Estate, 6-10 guests From US $832
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Lake Cottage on 3 acres w/350 sq. ft. deckn From US $255
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Wildlife Retreat in the Forest From US $534
         

9.6 (9 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow From US $458
         

Remote and Relaxing Cabin in the Berkshires From US $284
         

10.0 (92 Reviews)
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Ashmere Lakefront Apartment From US $184
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond From US $355
         

Charming Farmhouse - quiet, private & peaceful From US $224
         

A simple kind of paradise From US $227
         

10.0 (23 Reviews)
Other
  • Parking
  • Pool
  • TV
Pro Tip: Holidayinthehamptons makes it easy to compare the best listings on Holidayinthehamptons homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayinthehamptons homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Skyline Trail.

Weather in Skyline Trail

View the weather forecast for Skyline Trail before booking your Skyline Trail Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Skyline Trail Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Skyline Trail?
How many vacation rentals are available in Skyline Trail?

Currently, the total number of properties listed in 2026 is over 41 in the Skyline Trail area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Skyline Trail.