Ski-in/Ski-out vacation rentals in Connecticut

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Connecticut

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Home in Canaan

New place to stay

Bellhaven

Keep it simple at this peaceful and centrally-located haven. 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.

Guest favorite

Cottage in Pomfret

4.95 out of 5 average rating, 38 reviews

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)

Home in Plymouth

New place to stay

Direct waterfront lakehouse.

Wake up and watch the sunrise to the breathtaking mountain and lake views whether Autumn, Fall, Spring, or Summer. There's always a unique view and something to do around the lake and mountains. Watch from the upper or lower decks or step outside to your private dock and watch the sunsets while having cold drinks or sipping hot cocoa around the fire pit. Stare at the reflection of the sunset and moon, making memories. Forget your worries in this spacious and serene space with a wood stove.

Guest favorite

Rental unit in West Granby

4.9 out of 5 average rating, 130 reviews

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.

Cottage in Hampton

4.86 out of 5 average rating, 69 reviews

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!

Guest favorite

Home in Roxbury

5 out of 5 average rating, 63 reviews

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.

Home in Avon

4.94 out of 5 average rating, 33 reviews

Waterfront Riverside Retreat

A private, secluded retreat set on the historic Farmington River, 75 feet from the water with 500 feet of river frontage. This property listing has been updated to add the master bedroom and bathroom suite — so that it now includes 2 full bathrooms and 2 half baths. This location is available for people looking for a natural space to spend time with family and friends. It's also available to television and film production studios for set locations. (Special film rates apply).

Superhost

Private room in New Haven

4.82 out of 5 average rating, 17 reviews

Relaxing Room with Private Entry – “Africa Room”

Welcome to Tree View: fully furnished and nestled in a 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 are 2 low-to-the-ground twin-size beds, a table, 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.

Private room in New Milford

5 out of 5 average rating, 11 reviews

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.

Guest favorite

Private room in Cornwall

4.89 out of 5 average rating, 243 reviews

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.

Guest favorite

Home in Plymouth

4.97 out of 5 average rating, 34 reviews

Lakefront Serenity Getaway: Your Blissful Escape

Embark on a captivating vacation at our picturesque lakefront sanctuary in Plymouth, CT. Featuring 3 bedrooms, 2 baths, and mesmerizing lake views, this retreat promises pure bliss and relaxation. Nestled between the vibrant cities of NYC and Boston, it's an irresistible opportunity to immerse yourself in nature's allure and create lasting memories. Unwind, rejuvenate, and savor the beauty of a perfect getaway.

Superhost

Rental unit in Winsted

4.88 out of 5 average rating, 41 reviews

Peaceful country getaway from the hectic city life

Our Airbnb is not a hotel nor a resort, we are private citizens that help the community, in opening our home which was built in the early 19th Century. For those who need a place to stay for a short period of time with the comfort of home living. We don’t pretend or intend to be in the hotel business, so we are unable to meet everyone’s expectations, but we do our best with what we have. Thank you!