Holiday rentals in Darien

4.99 out of 5 average rating, 139 reviews

Flat in South Norwalk

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.

ValueLocationLayout

Superhost

A well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.

Home in Stamford

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.

LocationValueWifi

4.83 out of 5 average rating, 222 reviews

4.95 out of 5 average rating, 21 reviews

Historic Norwalk Home Near SoNo & NYC

Enjoy a cozy retreat in Norwalk with your family and friends! 5-min drive to Calf Pasture Beach, a highlight of the town with a skate park, playground, restaurant, and basketball court. Whole House Water Filtration + Alkaline Drinking Water Right next to SoNo, a beautiful coastal area with an aquarium and the main hub for restaurants Close to train to Grand Central (don’t worry, it’s quiet!) Full kitchen and private patio, ready for BBQ parking 500 Mbps WiFi (really fast) Tesla charger

FamilyLocationCleanliness

A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.

4.98 out of 5 average rating, 148 reviews

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.

LocationFamilyQuiet

Superhost

A spacious living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table is positioned on a patterned rug, with the kitchenette visible in the background. Soft lighting and light-colored walls contribute to a bright and inviting atmosphere.

Guest suite in Stamford

Beach Walk Haven: 1 BR Lower Level

Welcome to your charming lower level one-bedroom Airbnb, perfectly situated within easy walking distance to the beach. Step into your private sanctuary and feel instantly at home. Immerse yourself in the coastal vibes as you take leisurely walks to the nearby beach, where you can soak up the sun, feel the sand between your toes, and revel in the soothing sounds of the waves. Embrace the coastal lifestyle and create unforgettable memories during your stay in this conveniently located apartment.

ValueLocationParking

4.76 out of 5 average rating, 208 reviews

4.99 out of 5 average rating, 173 reviews

Guest house in Rowayton

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.

FamilyLocationBack garden

4.95 out of 5 average rating, 133 reviews

A cozy seating area features a wooden chair with a green cushion. Natural light floods in through the glass doors adorned with light yellow curtains, offering views of the garden outside. A patterned rug adds warmth to the space.

Cabin in Norwalk

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)

LocationValueKitchen

The spacious living room features a light-toned sectional sofa complemented by a wooden coffee table. Natural light enters through a nearby window, illuminating the neutral décor. A decorative plant adds a touch of greenery, while a dining area is visible through an adjoining doorway.

4.99 out of 5 average rating, 88 reviews

Cove Park Sunsets |Hot Tub/Fire Pit/BBQ/EV Charger

Located just a short train ride away from NYC, walking distance to Cove Island Beach Park and Chelsea Piers. Approximatly 1.7 mi from downtown Stamford and train station. Step into our modern, spacious retreat, offering 3 beautifully designed bedrooms, a convenient 1.5 bathroom setup, a private patio with a motorized awning, fire-pit, BBQ grill and hot tub. Apartment is loaded with all the amenities to make your stay enjoyable and convenient. Pets allowed approval required.

ValueLocationAir conditioning

4.98 out of 5 average rating, 121 reviews

A sunroom features light blue walls complemented by natural light from the large windows. Two rocking chairs are positioned beside a wooden table. Decorative mirrors reflect the cozy ambiance, while soft curtains frame the windows, providing a serene and inviting space.

Home in Stamford

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!

FamilyLocationDecor

4.92 out of 5 average rating, 53 reviews

The Pond House

Mid-century modern home with private pond in an exclusive neighborhood. Central AC and heat. Set on a spacious 0.7-acre lot. Just one hour from NYC by train or car (Rowayton & South Norwalk stations). Enjoy birdwatching and duck sightings from the large deck overlooking the pond. Peaceful cul-de-sac. Pet-friendly. Private office on the first floor plus a workstation in the main suite. Main bathroom features electronic shower and heated floors. Fully equipped kitchen.

LocationFamilyNearby

4.97 out of 5 average rating, 29 reviews

A modern kitchen features sleek white cabinetry, stainless steel appliances, and ample countertop space. A black gas stove and silver refrigerator are prominently displayed, while a sink and dishwasher are integrated into the design. Soft lighting enhances the bright and clean atmosphere.

Flat in Darien

Cozy Jr. bedroom in Darien

Nestled between Rowayton and Darien’s beaches, this one-bedroom retreat offers a perfect getaway from the bustling city life. As you step into your private entrance of this thoughtfully designed apartment, you will feel a sense of comfort and tranquility. The open floor plan seamlessly combines the living, dining, and kitchen areas. Whether you are visiting for business or pleasure, a good night's sleep awaits you on the Wink king sized bed.

ValueLocationKitchen

4.94 out of 5 average rating, 137 reviews

Home in Stamford

5BR Coastal Home, Walk to Beach, Private Yard

Make yourself at home in this bright 5-bedroom getaway just a short walk from Cove Beach and Park. Enjoy a private fenced yard, game room, fire pit and plenty of ways to spend time together—whether you’re here for a family trip, weekend with friends or an extended stay. Downtown Stamford is just a few minutes away, while the beach, waterfront trails, playgrounds and recreational areas are close enough to enjoy throughout your stay.

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Popular amenities for Darien holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Darien

A modern kitchen is equipped with stainless steel appliances and a large marble island. Four brown leather stools are arranged neatly at the island, illuminated by pendant lights above. Bright natural light enters through a window, enhancing the clean design.

4.96 out of 5 average rating, 48 reviews

Spacious Home Near Beach + Train Sleeps 10+ | Yard

FamilyLocationCheckout

5.0 out of 5 average rating, 25 reviews

Cottage in Westport

Nama-stay: sweet Saugatuck Shores beach cottage

FamilyLocationAccuracy

4.91 out of 5 average rating, 33 reviews

Modern Luxury 1BR | Heart of Downtown Stamford

LocationGetting aroundSleep quality

5.0 out of 5 average rating, 24 reviews

The exterior of the stone cottage is displayed, featuring arched windows and a sturdy roof. Surrounding trees exhibit autumn colors, enhancing the setting. A grassy area leads to the entrance, while a natural landscape offers a peaceful backdrop.

Home in New Canaan

Historic Stone House Recently Restored

LocationFamilyGetting around

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

4.95 out of 5 average rating, 73 reviews

Spacious. Water Views & Access. Steps to Beach.

FamilyLocationWifi

4.98 out of 5 average rating, 51 reviews

Guest house in Norwalk

Waterfront Getaway - Norwalk, CT

LocationFamilyNearby

The exterior of a two-story house is displayed with a traditional design featuring white siding and black trim. A welcoming front porch is flanked by neatly landscaped flower beds. A well-maintained lawn surrounds the property, with a driveway visible in front.

4.94 out of 5 average rating, 64 reviews

Family friendly

LocationValueWalkability

A serene skyline view captures the sun rising above the horizon, casting natural light across the landscape. Various rooftops are visible, including a building with a prominent dome. A clear sky showcases soft clouds, enhancing the tranquil morning atmosphere.