Guesthouse holiday rentals in Litchfield County

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

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).

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

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

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.

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!