Holiday houses in Weston

The Cozy Little Cottage

Charming guest apartment on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.

Private Guest Suite | Entrance, Bath & Parking

Private guest suite with a private entrance, attached bathroom, dedicated workspace, fast internet, and private parking. Located on a quiet 1.5-acre property in Wilton, CT, walking distance of ASML and close to Norwalk Corporate Park, downtown Wilton, restaurants, coffee shops, stores, parks, and the Norwalk train station. Owners live in a separate part of the house. Guests have private access and space. Pets are welcome, outdoor space for dog walks. Cats live here but do not enter the suite.

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

Tree Haven Loft, Grille, Firepit & Nature

Treehaven Loft—a bright, serene retreat in elite Weston, bordering vibrant Westport, CT. Soaring beamed ceilings, expansive windows framing majestic trees, and nature-inspired art create a peaceful, boutique-hotel vibe. Ideal for romantic getaways, creative escapes, or family fun. Enjoy a gourmet kitchen with espresso maker & wine fridge, cozy fire pit, and grilling area. Minutes from pristine beaches, concerts, dining, and shopping. Your perfect blend of tranquility and convenience awaits!

3‑Acre Weston Retreat w/ Pool & Basketball Court

Private 3-acre retreat in Weston, CT, featuring a heated seasonal pool, full basketball court, gas fire pit, and expansive wooded grounds. The dramatic double-height great room showcases soaring windows that bring the outdoors inside, while curated African artwork adds warmth and character throughout. Enjoy privacy, nature, and easy access to Compo Beach, Devil's Den, charming New England towns, and NYC. No children under 5. Maximum 8 registered guests. No early check-in. Strictly no parties.

Nature Retreat Airbnb

House located in beautiful and tranquil Redding, CT. Two floors with private deck. Main level: half-bath, cook's kitchen with a 4-person dining area, living room with flatscreen TV with an Apple TV and a view of nature. Living room convertible couch can sleep two small children or one adult. Upstairs: 2 bedrooms with full size beds, privacy blinds, bathroom w/ shower (no tub). If you want a getaway from the city, or just an escape then come to this quiet and private house in the woods.

Nature Lovers Guesthouse

This charming Guest House is a perfect city escape for enjoying nature, visiting friends and family, or conducting business. Located near amazing hiking, fishing, and parks, while just a 15-min drive to beaches, shopping, and dining. Located right on Route 53, the Guest House sits apart from the main Log Cabin, providing serene views of the garden and pond. You may even recognize this property from a Ralph Lauren ad or the 1975 film The Stepford Wives. PLEASE READ 'Other Details To Note.'

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

River Cottage in Weston, CT

Welcome to “River Cottage”, our enchanting private guest cottage in the picturesque town of Weston, CT, nestled on a riverfront property. Located about 45 miles from NYC, and 10 minutes from the lively town of Westport, our two-bedroom cottage is the ideal location for a relaxing few days, a business trip in the area or visiting family and friends. Perched near the tranquil Saugatuck River, the immediate area is a haven for hiking and trout fishing.

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.