Holiday rentals in Litchfield County

The oldest home in Litchfield.

You will simply fall in love with The Red House 1735! Cozy antique home adorned with vintage treasures. Conveniently located near everything the area has to offer. Walk across the street to White Memorial Conservation, with some of the most beautiful trails in Litchfield County. 5 minute drive to the town of Litchfield with quaint shops and restaurants. Bantam Lake, CT Wine Trails, Mohawk Ski Mountain, and so much more is within a short driving distance. We welcome you to enjoy our country oasis

Halo Hollow Haus - Litchfield Lake & Ski Haven

Rest, relax, and recharge in this serene and stylish space. Halo Hollow Haus is a lake house and ski lodge offering boutique vacation vibes and year-round country beauty. Nestled in the beautiful Woodridge Lake community, you'll enjoy lake life at its finest while just minutes away from all that Litchfield County has to offer. Enjoy classic New England towns, swimming, skiing, hiking, fishing, parks, golf, mountains, foliage, antiquing, vineyards, excellent restaurants, and cultural attractions.

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

The Cottage @ 228 Maple

This charming, fully equipped 2-story home is privately set at the edge of the woods. Five minute drive to the historic Litchfield Center, this gem is central to everything, making it easy to plan your visit. History walks, museums, restaurants, boutiques, antiques, wineries, distilleries, & farmers markets. Yearlong recreational activities -hiking, biking, birding, boating, skiing nearby at Bantam Lake, White Memorial, Mohawk Ski Area, Topsmead State Forest, Land Trust & Audubon Preserves.

Cozy Cottage |Quintessential CT | Pet Friendly

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

Litchfield Luxury Home w/Heated Pool

Escape to this fully renovated 4BR, 2.5BA estate on 12 private acres with sweeping views of Litchfield’s hills. Enjoy a heated pool (seasonal @ $50 per day upcharge), private gym, and walking trails. Inside, relax in beautifully furnished spaces with hardwood floors and New England charm. Just 3 miles from downtown Litchfield’s shops, dining, and hiking. Whether you’re sipping coffee while watching the sunrise or relaxing at sunset by the pool, the views are breathtaking year-round.

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

SerenityCT

New! Litchfield, Connecticut Nestled on 7 acres in the heart of a charming, quintessential New England town, our Chalet styled home offers a unique vacation rental. Enjoy the feel of nature without sacrificing the luxury of comfort. Experience rich history, nearby vineyards, hiking trails, breweries, nature and so much more!