Guest house holiday rentals in Fairfield County

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).

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

Lost in Decision Forest Guesthouse

A small 3-bedroom guest house. Ask us about the beach passes if interested. Please note that you do need a car to get around unless you are willing to walk 50 mins to the train station. There are always a few projects going on but I try to make sure they do not interfere with normal life and are reasonably reflected in the photos. I temporary gave up on trying to pick a color so you’ll see some things looking a bit unfinished.

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.