Holiday rentals in Lewisboro

Retreat in North Stamford

A great getaway retreat with a spa for your body and mind in a brand new 450 sq. ft. Studio private space with its own entrance and everything needed for a comfortable stay. You can create different light atmosphere. You can also enjoy having a relaxing spa session (in the same house where you are staying) to rejuvenate your face , body and mind. Treatments also available for pain and stress. (This is an additional service not included in nightly price. Please reach out to the host for details.)

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

Private farm cottage +hiking

Private home with large stone patio with access to over 4,000 acres of trails in Ward Pound Ridge. Owner lives on the property and is happy to introduce you to the horses Lincoln, Domino, and Forceti. The house has its own driveway and sits on two acres and is quiet and private. We have a great internet connection, with two working spaces set up in the house (1 in the bedroom and another in the kitchen) for remote work. Enjoy the scenery and tranquility of northern Westchester.

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

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

Casa Luna Lake Cottage

Enjoy a quiet, peaceful getaway at Casa Luna! Sits on a property with two separate cottages. Across the street from the lake and with numerous hiking trails and parks in the area. Enjoy a cozy fire at the cabin with the outdoor firepit. Only 4 miles to Le Chateau wedding venue. An easy 10-minute drive to Ridgefield, CT for groceries, tons of restaurants, and other activities. Close to numerous Metro North train stations for easy access to NYC.

Historic Hideaway - Lake Access

Welcome to “Stone Gate” our charming historic hideaway by the lake. The home, circa 1760s, boasts all the storybook charm you could dream of, combined with a functional and tasteful modern touch. Enjoy a glass of wine on the oversized patio, a quick walk to the lake for a swim or kayak adventure (just 300 feet away) or explore the area's many attractions, wineries and restaurants. A true country retreat awaits.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Charming Cottage in historic Bedford Village

“This place emanates why I would live here!” - Robert 7/24 Just a 5 min walk to historic Bedford Village this detached one-bedroom cottage is surrounded by 200yr old Maple trees on the property of a 1840's farmhouse. Experience the hamlets of Westchester only 39 miles north of Manhattan and less than 10 min to the Bedford Hills - Harlem North train station.