Vacation rentals 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.

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

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!

Garden Level 2 Bedroom Suite 5 Min to Westport

Welcome to your private garden-level retreat in Weston CT. An artfully designed, cozy, 2 bedroom suite. With its own entrance, secluded patio with wooded and peaceful surroundings, this curated space blends comfort, style, and serenity. Just minutes from Westport, it offers an award-winning mattresses, a cozy lounge area, organic coffee bar, high-speed WiFi, and more. Calm, clean, and thoughtfully designed. Guests describe it as peaceful, beautifully styled, and full of thoughtful touches.

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.'

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your AUTUMN GETAWAY at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

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.

3‑Acre Weston Retreat w/ Pool & Basketball Court

Escape to a private 3-acre retreat in Weston, CT, minutes from Westport. Enjoy the heated pool, full basketball court, gas fire pit, and dramatic double-height great room surrounded by nature. A summer note: we’re receiving many requests for parties and celebrations. We understand—it’s that time of year! But this is a private home, not an event venue. In keeping with Airbnb’s strict policy, no parties, events, or unregistered guests are permitted.

Spectacular Renovated Barn

Make memories at this unique and family/group -friendly place. Professional chefs kitchen, outdoor patio and large fenced in yard - very pet friendly. This dramatic home is a perfect retreat / multi-family. Quite street. Great open space for cooking and socializing. Soaring 11-foot ceilings, antique wood beams, working fireplace and walls of glass that flood the interior with natural light, historic character with contemporary functionality.