Vacation rentals in Darien

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Darien

  • Total vacation rentals

    Explore 60 vacation rentals in Darien

  • Nightly prices starting at

    Darien vacation rentals start at $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,990 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Darien vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Darien rentals

  • 4.8 Average rating

    Darien stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Darien

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
Apartment in South Norwalk
4.99 out of 5 average rating, 136 reviews

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.

Guest favourite
Home in Norwalk
4.93 out of 5 average rating, 14 reviews

Nice Colonial, EV Charger, Patio BBQ, SoNo, Beach

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

Guest favourite
A modern kitchen features white cabinetry and sleek stainless steel appliances. The spacious layout includes a large refrigerator, a built-in oven, and a dishwasher. Natural light enters through nearby windows, illuminating the stylish countertops and a decorative rug that adds warmth to the space.
Apartment in Stamford
4.94 out of 5 average rating, 143 reviews

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

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
4.83 out of 5 average rating, 217 reviews

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.

Top guest favourite
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.
Home in Norwalk
4.98 out of 5 average rating, 137 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.

Guest favourite
A spacious living area features a large, U-shaped sectional sofa with various cushions in neutral tones and accents. A wooden coffee table with a candle sits in front, while a wall displays a simple black and white 'LOVE' art piece, enhancing the cozy atmosphere.
Apartment in Stamford
4.96 out of 5 average rating, 203 reviews

Terra Hillside Suite | 3 Bed 2 Bath | Green Oasis

Enjoy this stylish 3-Bedroom apartment located near downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 25 minute walk. Washer and Dryer included in the unit. This unique place has a style all its own! 2rd Fl. Unit use stairs.

Top guest favourite
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
4.94 out of 5 average rating, 123 reviews

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)

Top guest favourite
Guesthouse in Rowayton
4.99 out of 5 average rating, 166 reviews

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.

Guest favourite
Guesthouse in Norwalk
4.98 out of 5 average rating, 45 reviews

Waterfront Getaway - Norwalk, CT

Enjoy a stylish experience at this prime location - ideal to explore, relax, or WFH. This beautiful seaside home has full direct waterfront views of the Norwalk Harbor and LI Sound from every room and a balcony. NYC is a quick ride away, with a train station just 0.4 miles away. Across the street is our lovely Veteran's Memorial Park with a route going to Calf Pasture Beach! Experience fine dining in SoNO, long lines at Mr. Frosty's Ice Cream, and more. You won't want to miss this experience.

Guest favourite
A spacious living room is highlighted by comfortable seating arranged around a soft area rug. Artwork depicting serene waters adorns the walls, while soft lighting from recessed fixtures enhances the ambiance. A dining area is visible in the background, creating an inviting space for relaxation.
Apartment in Norwalk
4.94 out of 5 average rating, 95 reviews

Van Zant Townhouse Apt #2

Enjoy a stylish experience at this centrally-located Brand New Townhouse. This Townhouse offers well over 1100 square feet of living space, which includes 2 bedrooms, 1.5 bathrooms, large living room, eat-in kitchen and laundry room, plus 2 cars garage. This convenient location offers 5 minutes walk to SONO bars and restaurants, SoNo Collection shopping mall, Metro North Train Station and waterfront parks. Minutes away from I-95 and 50 minutes away from NYC Grand Central on express train.

Guest favourite
A newly renovated cottage is set against a clear blue sky, featuring white siding and a sloped roof. The entrance is flanked by well-maintained shrubs and a gravel pathway, while two modern chairs are positioned on the patio, providing a relaxing outdoor space.
Guesthouse in Darien
5 out of 5 average rating, 9 reviews

Charming Cottage Near Beach/Town

Clean, sleek, and beachy—this newly renovated and professionally decorated cottage is the perfect coastal retreat. Located on a waterfront property within a private association, it offers charming interiors, modern comforts, and serene views. Just minutes from town and the beach, this adorable cottage blends style, privacy, and relaxation for the ideal getaway. Living room has 2 sofas; sunporch has 2 daybeds—(a big hit with younger guests), in addition to the queen bed in the main bedroom.

Guest favourite
A modern living area features a brown sofa and a black armchair, along with a sleek coffee table positioned on tile flooring. Natural light enters through glass doors, illuminating a decorative wall art piece depicting waves. A small dining table with two chairs is also visible.
Apartment in Norwalk
4.83 out of 5 average rating, 90 reviews

Cozy, functional, soothing

Welcome to a contemporary and comfortable apartment. Built to be relaxing yet functional, the home is spacious and ideal for couples or business travelers. Main highways are a few minutes away. A train station with direct trains to NYC is exactly 1 mile away. It's a great walk if you want to get your steps in. Bayly's Beach is a bike ride away. Various restaurants on the water are within a 1-mile radius (e.g. Sails American Grill, Rowayton Seafood).

Popular amenities for Darien vacation rentals

When is the best time to visit Darien?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Darien?

    Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Darien?

    Yes! Work meets play with ease at over 40 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Darien?

    Darien has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Darien?

    Experience the best of Darien with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Darien have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Darien have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.