Ski-in/Ski-out holiday rentals in Connecticut

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the Joab Griffin House. We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard

In the countryside of Connecticut, this charming cottage awaits anyone seeking an outdoor escape! Only 2 miles from James L. Goodwin State Forest, this vacation rental is ideal for cross-country skiing in the winter and hiking in the summer! You'll only be a short drive from sightseeing hubs like Brooklyn, Hartford, and the University of Connecticut in Mansfield! The home has 3 bedrooms, 1.5 bathrooms, a full kitchen, and a spacious yard that's great for outdoor activities in all seasons!

Twilight Dreams Farm

Twilight Dreams Farm is a 1786 Farmhouse that is 2,584 sq ft on 20 acres surrounded by 800 plus acres of land trust and adjacent hiking trails. It is rustic with many of the original features. The farm is home to 2 horses, 60 ducks, 2 cats, and numerous other wildlife. It has ponds, hay fields, walking paths along the perimeter of the property, and a stream. The property across the street is adjacent to miles of beautiful trails along the Shepaug River, which is known for fly fishing.

New Haven Game Room

Welcome to your home away from home in the vibrant city of Connecticut! Whether you're here for a short business trip or an extended stay, our space is designed to make your work-life balance both comfortable and productive making it an ideal choice for work travelers, students, faculty, and families alike. We’re dedicated to making your stay as comfortable as possible. Let us know if you need anything special to accommodate your work needs during your stay!

Litchfield County Ensuite Getaway

Nestled in a small valley in the foothills of the Berkshires in Litchfield County, This vintage farm house, Mabels Hollow Farm, is a beautiful, 15 acre location perfect for year-round getaways or vacations. Close to pristine crystal clear lakes for summer swimming, breathtaking fall foliage, cross country skiing on property and downhill nearby and running, hiking and biking in the spring. Close to Canterbury School and other private schools.

Cornwall Colonial w/ Queen Bedroom

A bucolic retreat near open fields with grazing sheep and forested hillsides, our house is only two hours from New York City, but feels like it’s in the middle of Vermont. Scenic drives, interesting shops and art and craft galleries, and delightful markets and restaurants are scattered throughout the quaint, historic towns of the Litchfield Hills. Hiking and other outdoor pursuits abound, from active sports to inspiring walks in nature.