Family-friendly vacation rentals in Darien

Costal Coziness: 1BR Retreat near beach.

Welcome to your cozy private getaway, nestled within a charming multifamily home just a short walk away from the beach. This delightful one-bedroom unit offers a serene retreat for your beachside escape. Relax in the spacious living room, complete with a comfortable seating area and a convenient kitchenette. The queen-size bed in the private bedroom ensures a peaceful night's sleep. Embrace the coastal vibes and enjoy the convenience of beachside living in this inviting and well-appointed unit.

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

S. Norwalk Studio Apt near the water!

Newly-built sunny studio apartment with separate eat-in kithchen and spacious bath, across the street from the water in the peaceful waterfront community of Shorefront Park in South Norwalk. 20 min walk to South Norwalk shops, restaraunts and the train station (65 min train ride to NYC). Private kepypad entrance, washer/dryer, eat-in kitchen, free off-street parking, wifi, central AC. 2 night minimum Please note the house next door may be under construction. Please inquire for current status.

Luxurious 1BR Downtown Stamford

Step into your luxurious haven in the heart of downtown Stamford, where opulence seamlessly meets comfort and indulgence becomes your personal mantra. From the impeccable design and luxurious amenities to the prime location, every moment spent here is a celebration of the finer things in life. Treat yourself to an extraordinary stay, crafting memories that will linger in your heart for a lifetime . Welcome to a world where luxury knows no bounds, and warm hospitality eagerly awaits your arrival

Gem by the water+ firepit and all fenced backyard

An episode of The Curious Case of… was filmed right here at the property. Stay where the cameras rolled and experience the same atmosphere that caught the producers’ attention. One block away from the water & 3 blocks away from Dolphin Cove. Enjoy walking and site-seeing. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. The house has also a lower-level unit.

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.

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)

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.

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

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Seashell Bungalow - located in Stamford, just a stone's throw from NYC. Less than a 2-minute walk from the beach. Perfect for those looking to enjoy the tranquility of the beach with the city life nearby. Outdoor dining area - perfect for summer evening relaxation. Fully equipped for fun and adventure - paddle boards and various games available. Ideal for family vacations or a friends’ getaway. Book your stay today and enjoy an unforgettable beachside adventure!

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

☆Charming Studio - Private/Self Check-In/Parking☆

Enjoy a restful stay or shorten your commute in this cozy studio with easy access to highways, shops, and restaurants. The studio has a private entrance and onsite parking. It also has fast internet, a laptop-friendly workspace, and a kitchenette. Perfect for business travelers or 1-2 people. Pets are welcome with a non-refundable fee. ***Please read the entire listing prior to booking including “other things to note”***