Places to stay in Canaan

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

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Charming CT Country Farmhouse for 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.

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Nature Cottage w/ Private Path to River Access

Summertime in 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.

Cottage with a Waterfall View

Fall asleep to the sound of a waterfall and babbling brook outside your bedroom window in this historic former flax mill known as St. John's Mill. The cottage is newly renovated and features a well equipped kitchen, sofa where you can put up your feet and gaze out the living room window at the dam and waterfall, and a private grill and terrace overlooking Guinea Creek. Located along a scenic route convenient to Kent, Millerton, Salisbury & Amenia.

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill