Photo by Tim Rousseau

Darien vacation rentals

We found 403 vacation rentals — enter your dates for availability

Discover a selection of 15 homes and other vacation rentals in Darien that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.
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Find out more about Darien

Find out more about Darien

Why visit Darien

  1. Picturesque Parks: Discover stunning parks ideal for picnics, hiking, and outdoor activities.
  2. Beautiful Beaches: Relax on inviting beaches perfect for sunbathing and family fun.
  3. Charming Neighbourhoods: Explore delightful streets filled with beautiful apartments and local charm.
  4. Cultural Experiences: Engage in cultural activities that cater to all ages and interests.
  5. Variety of Accommodations: Choose from cozy cottages to stylish apartments for a perfect stay.

Popular types of accommodation in Darien

Planning a getaway to Darien? You're in for a treat! Explore a fantastic selection of vacation rentals, including houses, cozy cottages, and stylish apartments. Whether you’re looking for spacious house rentals or a quaint apartment in Darien, our platform offers an array of options to suit your needs. Enjoy transparency, savings, and peace of mind as you find the perfect home away from home.

  • Houses: The top choice for visitors, offering spacious and comfortable settings perfect for families or groups seeking a home-away-from-home experience.
  • Apartments: A popular option for those looking for convenience and easy access to local amenities, ideal for both short and extended stays.
  • Cottages: Charming and quaint, these rentals provide a cozy atmosphere for a relaxing getaway.
  • Condos: A great choice for travelers wanting modern comforts in a vibrant community.
  • Villas: Luxurious accommodations that offer an upscale experience, perfect for those seeking indulgence during their vacation.**

Top attractions in Darien

Darien, Connecticut, is an ideal destination for outdoor enthusiasts and families seeking a city-themed vacation. With stunning parks, inviting beaches, and serene nature preserves, there’s plenty to explore. The area's attractions offer a mix of outdoor activities and cultural experiences that cater to all travellers, ensuring a memorable visit for everyone.

  1. Historic South Norwalk: A charming district that boasts rich cultural heritage, featuring beautifully preserved buildings, quaint shops, and delicious dining options. It's a great place to explore local history and enjoy unique art galleries.
  2. The Glass House: An architectural marvel designed by Philip Johnson, this museum offers a stunning view of modernist design. The transparent structure harmoniously blends with its natural surroundings, providing a unique cultural experience.
  3. Greenwich Avenue: A vibrant shopping street lined with upscale boutiques, cafes, and restaurants, capturing the city's lively atmosphere. Perfect for leisurely strolls, it offers a taste of local life and culture.

Things to do recommended for couples

For a romantic getaway in Darien, catch a concert at Levitt Pavilion for lively entertainment, indulge in a rejuvenating treatment at Hand & Stone Massage and Facial Spa, and savor exquisite wines at Del Vino Vineyards, all while enjoying a charming atmosphere perfect for couples.

Things to do recommended for families

During your family vacation in Darien, enjoy thrilling activities at Chelsea Piers, relax at Waveny Park, and explore the stars at Rolnick Observatory. Each destination offers unique experiences, perfect for creating lasting memories together.

Things to do recommended for groups

Explore the Stamford Town Center for shopping and entertainment, just 6.4km from Darien. Enjoy a show at the Stamford Center for the Arts, also 6.4km away, or visit the Springdale Shopping Center, located 4.8km from Darien, for a family-friendly shopping experience.

What do I need to keep in mind when booking a vacation in Darien

When planning your trip—whether you're going with a group, family, bringing along pets, or seeking extended stays—be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Darien with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options, and so much more, on Vrbo.
  • Traveling to Darien with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to take into account how close you are to attractions that are family-friendly.
  • Taking your pets with you to Darien: For many families, a trip isn’t truly fulfilling without their furry companions. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Darien: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Darien

Darien, Connecticut, offers a delightful mix of outdoor adventures and family-friendly activities. Explore charming neighborhoods with beautiful apartments, or venture to nearby cities for a taste of their unique atmospheres, from romantic spots to historical landmarks. With its welcoming vibe and scenic parks, Darien is perfect for a relaxing getaway, making it an ideal base for discovering the best of coastal New England.

  • Stamford: Located 6.4km from Darien, Stamford is a vibrant city that offers a rich blend of family-friendly activities and urban experiences. Visitors can enjoy shopping in the bustling downtown area, catch a show at one of the local theatres, or explore educational institutions that host various events. Notable landmarks include the tourist precinct and the lively Modern Square, which serve as perfect spots for dining and entertainment. Stamford’s accessibility and array of attractions make it a must-visit destination for anyone looking to immerse themselves in city life.
  • Norwalk: Also situated 6.4km from Darien, Norwalk is known for its family-oriented atmosphere and outdoor adventures. The city features a variety of shopping areas and offers access to a popular casino for a bit of excitement. Attractions such as the scenic beaches and historic sites provide a wonderful backdrop for relaxation and exploration. Norwalk’s blend of recreational opportunities and cultural experiences makes it an ideal spot for those seeking both adventure and leisure.
  • Rowayton: Just 3.2km from Darien, Rowayton is a charming village that entices visitors with its beautiful scenery and romantic ambiance. Outdoor enthusiasts will find plenty of recreational areas, and the nearby ski fields and resorts offer seasonal fun. The picturesque beaches and serene lakes are perfect for a peaceful day out or a romantic stroll. Rowayton's inviting atmosphere and natural beauty create the perfect setting for a relaxing getaway.

Best time to go to Darien

If you're planning a trip to Darien, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.5°F (-0.3°C)Light RainMostly SunnySlightly LowSlightly Low
February32.7°F (0.4°C)Light RainMostly SunnyAverageSlightly Low
March39.4°F (4.1°C)Light RainMostly SunnySlightly HighSlightly Low
April49.6°F (9.8°C)Light RainMostly SunnySlightly HighAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June68.5°F (20.3°C)Light RainMostly SunnyAverageSlightly High
July75.6°F (24.2°C)Light RainMostly SunnySlightly HighSlightly High
August74.5°F (23.6°C)Light RainMostly SunnyAverageSlightly High
September67.8°F (19.9°C)Light RainMostly SunnyAverageAverage
October57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
November45.9°F (7.7°C)Light RainMostly SunnySlightly LowAverage
December37.9°F (3.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or keep track of your bookings. The properties you’ve saved or reserved are thoughtfully categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Darien

The island views and parks create a pretty picture of Darien. This city is well-known for its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Darien

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Darien has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Chelsea Piers (2.9 mi / 4.7 km)
  • Norwalk Maritime Aquarium (3.1 mi / 5.1 km)
  • Bayville Adventure Park (13.1 mi / 21.1 km)
  • Rye Playland (13.1 mi / 21.2 km)
  • Del Vino Vineyards (13.6 mi / 21.9 km)
  • Fairchild Wheeler Golf Course (15 mi / 24.2 km)

Exploring the natural features in Darien

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Darien is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Cove Island Park (2.7 mi / 4.3 km)
  • West Beach (3.9 mi / 6.2 km)
  • Calf Pasture Beach (4 mi / 6.5 km)
  • Old Mill Beach (5.8 mi / 9.3 km)
  • Compo Beach (6.3 mi / 10.1 km)
  • Greenwich Point Park (7.8 mi / 12.6 km)

Transportation to and around Darien

Fly into Westchester County Airport (HPN), the closest airport, located 12.3 mi (19.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 18.5 mi (29.8 km) away.

If you're traveling by train, make your way to Darien Station or Noroton Heights Station and explore the city from there.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Darien?
Based on our research, houses are the most desirable vacation property type in Darien. But of course, everyone’s idea of the perfect stay will differ. Vrbo has vacation homes in a variety of shapes and sizes, so you’re bound to find the perfect match.
How much does it cost to rent a vacation rental in Darien?
Property type, season and length of stay are some of the conditions that can affect the price of a vacation home. Simply enter your dates of travel to find your dream escape. From cozy cabins to sprawling villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Darien?
The average price for a vacation home close to the beach in Darien will depend on when you’re going and the type and size of property you’re searching for. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then use the handy filter tool to select the number of bedrooms and amenities essential to you, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Darien?
Pack up a suitcase for your canine companion because Darien has 11 vacation rentals that roll out the welcome mat to pets. Let your four-legged friend enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Darien?
Check the “pool” box in our handy filter tool and choose from four houses with private pools in Darien on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your Vrbo vacation property comes with its own swimming pool.
What are popular rental amenities in Darien?
Tennis, a lake view and a firepit head the list of most popular rental amenities in Darien. Whether you’re taking a trip alone, with your better half or a group of family members, Vrbo will help you find a vacation rental that suits your style with all the options you need.
Are there large group vacation rentals in Darien?
With four properties that can host 10 guests or more in Darien, there’s no need to keep your invite list short. From family vacations to special events like birthday and Christmas parties, Vrbo will help you find a large group rental to match the occasion.
Are there vacation rentals in Darien that welcome kids?
Darien has 11 family-friendly vacation homes to choose from. And securing a stay that welcomes kids is a cinch with our “Properties good for families” filter. On top of having the whole place to yourselves, you’ll enjoy access to amenities and perks like bunk beds, kitchens and yards.
What are the top attractions for families in Darien?
Keep your kids occupied at these awesome family-friendly attractions in Darien:

  • Compo Beach
  • Norwalk Maritime Aquarium
  • The Maritime Aquarium

Are there vacation rentals with WiFi in Darien?
Darien has five vacation rentals with WiFi, so you can stay connected while on vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to updating your social media, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Darien?
Darien has 11 vacation rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo with this amenity, enter your desired travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Darien?
The minimum age permitted can differ between properties on Vrbo, so be sure to check the rules of the vacation home in Darien you want to book. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Darien for?
The amount of time you can rent a Darien vacation rental for is down to each property. Just enter your travel dates to view available options that offer extended stays. They come with all the things you need to make your extended getaway more enjoyable such as laundries and air conditioning. Some Vrbo vacation properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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