Holiday rentals with outdoor seating in Sharon

Cabin Nestled in the Litchfield Hills

Cozy, curated cabin in NW Connecticut—just over 2 hrs from NYC by car or train. Nestled above the Housatonic River, it’s a place to hike, antique, or do nothing at all. Watch wild turkeys, deer, rabbits, and the occasional fox wander through the yard. Toast s’mores by the fire pit, then stargaze beneath a wide, quiet sky. The Appalachian Trail and some of the best hikes in the Northeast are just steps away. A peaceful escape in every season—recharge with nature, friends, or the stillness itself.

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

Vibrant, secluded dome home in Litchfield County!

Positive vibes, tranquility and refuge await! Reconnect with nature at this unforgettable escape on 3+ acres. Allowing an open flow of light, atmosphere, and energy, dome homes can offer a spiritual experience, and this property offers all that times two. Consider these naturally efficient domes your break from it all 10 minutes or less to; Skiing (Mohawk Mt.) Lake Waramaug Appalachian Trail Housatonic River Ct Wine Trail Kent Falls Antiques, art galleries, farmers markets, brewery, & more

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Nature Cottage w/ Private Path to River Access

Summertime in beautiful Sharon! Comfortable, rustic cottage with fire-pit, wood-burning stove, large deck for star-gazing, 4 acres, a brook and private path to 200' Housatonic River frontage. So cozy! In lovely Litchfield Hills, covered bridges, lake swimming, restaurants, the Appalachian trail and hiking trails, ski areas, Audubon Center, Clarke Outdoors tubing/ kayaking and Ellsworth Farms fruit picking. Near Millerton, Kent, Great Barrington. Lake beach pass included in the rental.

Romantic Sunset View, horse country, nature & WiFi

Luxurious private suite with stunning 50-mile Hudson River Valley sunset views! Horse country, ideal for horse and nature lovers and 200+bird species. Private entrance, kitchen, bathroom, HEPA filters, 500Mbps WiFi, 55” 4K TV. Enjoy a private pond for picnics, luxurious cushioned chaise lounges, another private deck and dock, table & chairs, firepit, badminton on 25 acres. Stargaze & delight in fireflies! Relax on the deck with crisp mountain air. Near picturesque towns.

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!