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.

Salty Kisses Cottage Relax

Salty kisses beach cottage is simply adorable. The perfect getaway. Your happy place, always fresh linens, tasteful coastal decor. Direct water views Beach access across street Amazing sunrise and sunsets. At the end of the road is Silver Sands State Park with showers and food. Walk on the boardwalk to Walnut Beach. Live music, milford creamery, bees knees, pizza, lazy lobster and specialty stores. We have a lovely backyard for grilling and chillin. Downtown & Lisman landing only 1-2 mile walk.

Salty Kisses Beach Cottage Milford CT

Salty kisses cottage. Bright clean &Cozy. The perfect getaway. Wake up & enjoy sunrise and catch the sunset on the beach. Beach access across street. Public beach Silver Sands Park@ end rd. 2 miles stretch of beach. Enjoy Lobster rolls, ice cream parlors, marina fresh juice. Live music downtown. Scenic bike route. Bring you Water shoes walk out to famous Charles Island Bird lovers? Private yard w grill, dining table, sundeck, hammock, corn hole. Wifi, Ac, outdoor shower. Close to Tydes/ Yale

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!

Full size bed, abundant storage, excellent wifi

Welcome to Tree View: fully furnished and nestled in a quiet, safe neighborhood! It is an environmentally conscious and LGBTQA+-friendly home, with a welcoming, accepting, and relaxing atmosphere. Immerse yourself in a clean, quiet space that prioritizes your comfort and well-being. There is a full-size bed, a small table for remote working, and excellent Wi-Fi. Any questions? Message me! Please note - I am IMMUNE COMPROMISED and thus can only host people who are VACCINATED and BOOSTED.

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.

Perfect for Large Groups | Monthly Stays Welcome

Welcome to our fully furnished home designed for your extended stays. Whether you're a travel nurse, contractor, visiting professor, or relocating to the area, this home offers comfort, space, and everything needed for longer stays. Conveniently located near major hospitals, universities, and highways, making commuting easy. Ideal for guests working in the New Haven, Connecticut area including staff at Yale New Haven Hospital and Yale University. Monthly stays welcome.

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

3 minutes to Ski Sundown. 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. After hitting the slopes at Ski Sundown, you can soak in the hot tub and enjoy billiards. The summer affords fishing, hiking, golfing, tubing or boating, leaving you rested and restored.

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.

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. I think you’ll love it!