Holiday houses in Roxbury

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Breezy Crest cozy, private retreat 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!

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Bright Mid-Century Modern Retreat-90 min from NYC

Mid-Century Modern, newly renovated 3 bedroom, 2.5 bath located on a secluded road. Inground heated pool & mature landscaping. Enjoy Sonos inside and out. Light shines into the living room, vaulted ceiling, wall of windows and sliders to a wooden deck overlooking the pool. Dining room with floor-to-ceiling windows and skylights. 2 bedrooms and 2 full baths on the main level; a 3rd bedroom with balcony, and a half bath. Electric charging station. Pool is open for the season.

Serenity in the Roxbury Woods!

Perfect cozy hideaway for families, writers, artists, couples, digital nomads or anyone seeking a peaceful, serene retreat in the woods! Set at the end of a private street, far back from the road, lies your 3BR, 2.5BA oasis with every amenity you can ask for! High-end appliances, blazing-fast wifi, soaking tub, Viking/Subzero chef's kitchen, all set on 8 quiet acres. The only sound you'll hear is the birds (and the occasional coyote howl at night). Inquire today!

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working (in progress) farm bordered by 155 acres of protected land trust with marked hiking trails. Southford Falls and Kettletown State Park are within minutes for fishing, picnicking, and hiking. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Custom industrial farmhouse Apt in Washington Dpt

Cozy and quiet one bedroom suite with a full kitchen. This space is on the 2nd floor over an attached garage with an entrance separate from the main house. It is newly constructed and has its own heat and AC, complete kitchen, full bath with shower and king sized bed. Just around the bend from Steep Rock Land Preserve and walking trails, and convenient to the center of town with galleries, restaurants and shops.

Roxbury Cabin Retreat

Take it easy at this unique and tranquil getaway. Escape to this charming cabin nestled on 10 acers of tranquil Roxbury, CT woodland. Tucked away down a secluded gravel road, this rustic retreat offers a peaceful escape from the hustle and bustle of city life. Enjoy the serenity of nature, unwind on the porch, and explore the surrounding woods. Perfect for a quiet getaway or a romantic retreat.