Ski-in/Ski-out holiday rentals in Connecticut

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the most beautiful area of CT! 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.

Quiet rm. with private entrance, at edge of woods

As a postgrad., lecturer, MD, or other professional, you’ll appreciate the Africa Room with its excellent Wi-Fi, and peace and quiet. It has 2 twin beds, a table and 2 chairs, sink, fridge, microwave, coffee maker, and air fryer. The backyard deck has excellent Wi-Fi, with woods and wildlife mere feet away. A 15-minute car ride from Yale Campus and downtown, my house is in a quiet and very safe neighborhood, environmentally conscious and LGBTQA+-friendly, with a welcoming and homey atmosphere.

Little House in the Big Woods - Tennis Court

The Little House is a small historic (pre-1800) fully furnished and equipped guesthouse on 145 private acres of secluded fields & woodlands adjacent to hundreds of acres more of preserved land and state parks in the Quiet Corner of Connecticut, 3 hour's drive from Ny, 1.5 hrs from Boston & 45 min from Providence/Hartford. It comfortably sleeps four people, and is also equipped for small children (“Pack and Play”with sheets, antique high chair provided and extra age-appropriate toys available)

Bellhaven

Keep it simple in the East wing of this 220 year old home. There are two full acres of beautiful land and space to bird or wildlife watch while relaxing in peaceful Canaan. We are two minutes from the Massachusets state line and Berkshires. There are nearby ski slopes, the Housatonic River and many bike and hiking trails. There is a selection of delicious local restaurants and a very lovely Main Street strip with a number of shops. Stop and Shop and Walgreens are nearby for quick essentials.

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.

Game Room near Yale

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!

Idyllic Cornwall Ski House

Discover your perfect getaway at this newly renovated, designer retreat nestled at the base of breathtaking Mohawk Mountain in Upstate Connecticut. Thoughtfully designed with high-end finishes and furnishings, this home offers the ultimate combination of style and comfort for a relaxing escape in every season. Wake up to scenic mountain views, thoughtfully curated to make you feel right at home. Perfectly located to all the best this area has to enjoy.

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.

Blackberry Cottage

Enjoy our peaceful (pet friendly) home, just a short drive to the center of Norfolk. Great for friends and/or family visits. Board games, puzzles and books inside for all; fire pit outside. Front & side decks, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. But, I think you’ll love it!

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.

Cornwall Colonial w/ Double 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.