Vacation rentals in Darien

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Top-rated vacation rentals in Darien

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

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Guest favorite
The living area features a neutral color palette with a contemporary couch and a low coffee table. A bar-style dining area with high stools is visible, complemented by a 42-inch Roku TV mounted on the wall. Natural light enters through a window, enhancing the inviting ambiance.
Apartment in Norwalk
4.91 out of 5 average rating, 357 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Top guest favorite
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, 127 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

Guest favorite
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
4.76 out of 5 average rating, 188 reviews

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.

Top guest favorite
A modest wooden house features large glass doors that lead to a spacious deck. The surrounding green lawn is complemented by well-kept shrubs and trees. Sunlight casts a warm glow on the exterior, highlighting the structure's simple charm.
Guesthouse in Rowayton
4.99 out of 5 average rating, 154 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.

Top guest favorite
Home in Wilton
4.97 out of 5 average rating, 144 reviews

The Cozy Little Cottage

Charming guest apartment on our property 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, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Top guest favorite
Apartment in South Norwalk
4.99 out of 5 average rating, 108 reviews

S. Norwalk 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. 15 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. Please note the house next door may be under construction. Please inquire for current status.

Guest favorite
The exterior of a red-brick building is featured, showcasing large black doors with decorative accents. Planters with greenery are placed on either side of the entrance. An iron fire escape extends above the doorway, while a flag hangs on the right side of the image.
Apartment in Wall Street
4.97 out of 5 average rating, 154 reviews

"Triplex Historic Beauty" with Seasonal Garden

Featured on the History Channel hit TV series "American Pickers"! Come join us at the head of the harbor in historic downtown Norwalk "Wall Street" neighborhood. This cozy second floor rental has been tastefully decorated with new and old. In addition to the photo descriptions we have included a floor plan for review. Please note the neighborhood is a working waterfront during the day and the Danbury active train line runs behind the building which adds to the character .

Guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 114 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest favorite
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
4.84 out of 5 average rating, 196 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. 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. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Guest favorite
A spacious bed is adorned with soft neutral linens and decorative pillows in warm tones. Light-colored side tables with lamps are placed on each side, and framed beach photographs are displayed on the wall above. A mirror reflects the inviting atmosphere in the room.
Apartment in Stamford
4.96 out of 5 average rating, 113 reviews

Cozy King BR | Walk to beach | Close to downtown

Welcome to the Lounge on Webb! Your cozy, little private oasis! It’s the perfect stay located just 10 minutes from Stamford’s downtown area and walking distance to Cove Beach and Chelsea Piers. Conveniently located just 40 minutes from NYC by train or car, you can spend your day exploring the Big Apple! Whether you’re here for business or leisure, this apartment provides the perfect blend of comfort and convenience!

Superhost
A bedroom is presented with a large window providing natural light, framed by dark curtains. The spacious bed features a patterned blanket, while a plush bench sits at the foot of the bed. A ceiling fan offers comfort, and wall art adds a decorative touch.
Apartment in West Side
4.85 out of 5 average rating, 108 reviews

Stamford’s Island Inspired Efficiency

This island-themed efficiency apartment offers comfort, style and convenience. After waking up on the memory foam mattress and before enjoying all the conveniences that downtown Stamford has to offer, or taking the nearby train to Manhattan, start your day by waking up to turquoise waters and seashells, sipping on different flavors of coffee or tea, and snacking on the light breakfast items provided.

Superhost
A cozy living area is present, featuring a neutral-colored sofa draped with an orange throw. A round glass coffee table is positioned in front of the sofa, set on a patterned area rug. Natural light filters through sheer curtains, illuminating the blue walls decorated with artwork.
Apartment in Glenbrook
4.78 out of 5 average rating, 206 reviews

Downtown "Blue Nest" apartment

Cozy, adorable, updated and fully decorated 1 bedroom apartment in a downtown building with garage & 24 hours security. Equipped with everything you might need. Come stay with us and discover Stamford through the eyes of a local talented artist. There are certain things about the building that I can't change - please read the whole description before booking

Popular amenities for Darien vacation rentals

When is the best time to visit Darien?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,643 GYDG$29,035 GYDG$32,377 GYDG$31,750 GYDG$32,585 GYDG$33,421 GYDG$31,959 GYDG$29,243 GYDG$27,363 GYDG$29,243 GYDG$32,585 GYDG$28,408 GYD
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Frequently Asked Questions

  • Where should I stay in Darien?

    Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in West Norwalk, over 290 vacation rentals in Noroton Heights, and over 460 vacation rentals in Tokeneke.

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

    Yes! Work meets play with ease at over 30 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 Darien vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Darien, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Darien have air conditioning?

    Absolutely! We offer over 10 apartment 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.

  • Are there family-friendly house rentals in Darien?

    Darien has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Darien?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 G$10,444 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Darien vacation rentals include wi-fi 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!