Ski-in/Ski-out holiday rentals in Connecticut

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 private guesthouse on 145 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.

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 Yale 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!

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.

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.

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

Unwind above tranquil waters, marinate in the pool, bundle beneath the blanket as the crackling fire radiates warmth, savor freshly roasted coffee perched on the mountain, unify with nature or imbibe libations with friends, this property affords serenity for all. Steps from skiing at Ski Sundown, fishing, hiking, golfing, tubing or boating, you will depart rested, restored and renewed.