Darien holiday lettings

We found 436 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Darien that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Darien

Showing deals for:20 Mar - 27 Mar

Image gallery for Updated Farmhouse Retreat

Exterior
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Updated Farmhouse Retreat

Wilton

8% off
Price is £7,540
for 7 nights, 1 room
£1,077 per night
includes taxes & fees
Updated Farmhouse Retreat

Find spaces that suit your style

Why visit Darien

  • Stunning Beaches: Darien boasts beautiful coastal spots, perfect for families to relax and enjoy the sun.
  • Outdoor Activities: Explore numerous parks and nature reserves, offering hiking, picnicking, and recreational activities.
  • Charming Neighbourhoods: Wander through quaint streets filled with history, local shops, and a warm community vibe.
  • Diverse Accommodation Options: Choose from private homes, cottages, and well-equipped apartments to suit all budgets.
  • Family-Friendly Attractions: Engage in various cultural experiences and activities tailored for visitors of all ages.

Popular types of accommodation in Darien

Planning a getaway to Darien? The exciting part is selecting your ideal accommodation. Discover a variety of options, including houses, charming cottages, and well-equipped apartments. Our comprehensive listings of holiday rentals in Darien ensure you find the perfect rental home that suits your needs and budget. Enjoy a memorable stay with transparency and savings at the forefront of your experience.

  • Houses: The top choice for holiday rentals in Darien, ideal for families or groups seeking a comfortable and spacious stay.
  • Apartments: A popular option for visitors, offering convenient and self-contained living spaces for couples or solo travellers.
  • Cottages: Charming and quaint, these rentals provide a cosy atmosphere, perfect for a peaceful getaway.
  • Condos: A modern choice featuring shared amenities, suitable for those who enjoy a community feel.
  • Villas: Luxurious accommodations that offer ample space and upscale features for a memorable holiday experience.**

Top attractions near Darien

Darien, Connecticut, is perfect for outdoor family holidays with a city vibe. Visitors can explore a variety of attractions, including urban parks, beautiful beaches, and nature reserves. These points of interest offer a delightful mix of outdoor activities and cultural experiences, making it an ideal destination for families and those seeking to immerse themselves in the local environment.

  • Historic South Norwalk: A charming area steeped in history, featuring beautifully preserved architecture, boutique shops, and delightful eateries. Immerse yourself in the cultural vibes as you explore its unique galleries and local events, just 1.9km from Darien.
  • The Glass House: An architectural marvel and museum designed by Philip Johnson, showcasing modernist design and stunning landscapes. Experience the fusion of art and nature, located 3.7km away from Darien.
  • Compo Beach: A picturesque sandy beach perfect for sunbathing, swimming, and picnicking. Enjoy the vibrant beach vibes and scenic views, just 3.7km from Darien.

Things to do recommended for couples

Ready for a romantic getaway in Darien? Enjoy a captivating concert at Levitt Pavilion, indulge in soothing treatments at Hand & Stone Massage and Facial Spa, or savour exquisite wines at Del Vino Vineyards. Each experience offers a unique blend of romance and relaxation, perfect for couples.

Things to do recommended for families

During your family vacation in Darien, you can experience the sporty atmosphere at Chelsea Piers, relax in the tranquil surroundings of Waveny Park, and enjoy a delightful visit to the Rolnick Observatory, perfect for some family entertainment and stargazing adventures.

Things to do recommended for groups

Explore Stamford Town Center for a vibrant shopping experience, or immerse yourselves in culture at the Stamford Center for the Arts. For a more relaxed outing, visit Springdale Shopping Center, perfect for family-friendly activities and local dining.

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

When you’re planning a trip with a group, family, or pets, or if you’re interested in extended stays, it’s essential to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Darien with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all these options and more on Vrbo.
  • Traveling to Darien with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, while also looking for suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Darien: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Darien: If you're in search of holiday rentals offering savings for stays of a month or more, you've come to the perfect destination. By using the appropriate filters, you can effortlessly discover and secure great deals on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Darien

Darien, Connecticut, offers a delightful blend of outdoor activities and family-friendly attractions, making it an ideal holiday destination. Visitors can explore charming neighbourhoods and nearby cities, immersing themselves in a vibrant atmosphere filled with history and warmth. From family homes for rent to picturesque parks, there's a wealth of experiences awaiting you. Whether you seek a romantic getaway or a friendly local vibe, Darien promises a memorable and diverse travel adventure.

  • Stamford: Stamford is a vibrant city located 2.5km from Darien, offering a delightful mix of family-friendly activities and urban exploration. Visitors can enjoy a bustling shopping area, catch a show at the local theatre, or engage in educational experiences. The city's attractions include the popular tourist precinct and Modern Square, where you can find an array of dining options and cultural events. Stamford’s parks and outdoor spaces provide lovely spots for relaxation and recreation, making it a well-rounded destination for those seeking both city life and outdoor adventures.
  • Norwalk: Norwalk, situated 2.5km from Darien, is an inviting city perfect for families and outdoor enthusiasts alike. The area boasts beautiful beaches, including family-friendly spots ideal for a day of sun and sand. Visitors can explore historic sites and enjoy shopping in charming local boutiques. Norwalk is also known for its educational attractions, making it a great destination for families. With recreational options, including skiing during the winter months, this city offers a varied experience that combines both cultural and outdoor activities.
  • Rowayton: Just 1.2km from Darien, Rowayton is a picturesque village that captivates visitors with its scenic beauty and romantic atmosphere. This quaint community is ideal for outdoor lovers, offering a range of recreational activities, including access to a lovely beach and a tranquil lake. Rowayton’s charming surroundings are perfect for leisurely strolls or picnics, making it a delightful spot for couples and families seeking relaxation amidst nature. The village’s small-town charm, combined with its stunning waterfront views, makes it a must-visit when exploring the region.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Are you hoping to save on your next holiday? Being flexible with your travel dates can be beneficial, as prices do vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of accommodation.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new getaways, continue with your existing arrangements, or review and organise your bookings. Your saved or booked properties are now categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/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 holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Darien

Are you hoping to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Darien a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Chelsea Piers (2.9 mi / 4.7 km)
  • Norwalk Maritime Aquarium (3.1 mi / 5.1 km)
  • Hand & Stone Massage and Facial Spa (4.1 mi / 6.6 km)
  • E. Gaynor Brennan Golf Course (4.9 mi / 7.9 km)
  • Stanwich Club (8.9 mi / 14.2 km)
  • Bayville Adventure Park (13.1 mi / 21.1 km)

Exploring the natural features in Darien

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Darien is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Cove Island Park (2.7 mi / 4.3 km)
  • Cummings Park Beach (3.7 mi / 5.9 km)
  • West Beach (3.9 mi / 6.2 km)
  • Calf Pasture Beach (4 mi / 6.5 km)
  • Old Stamford Road Bird Sanctuary (4.4 mi / 7.1 km)
  • Compo Beach (6.3 mi / 10.1 km)

Transport to and around Darien

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 12.3 mi (19.7 km) from the city centre. 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 travelling by train, make your way to Darien Station or Noroton Heights Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Darien when booking a holiday rental?
When considering a holiday rental in Darien, Connecticut, a popular area to stay is the Tokeneke neighbourhood. This charming locale is known for its picturesque waterfront views and a relaxed, family-friendly atmosphere. Here, visitors can enjoy the beautiful Tokeneke Beach, which offers sandy shores and a serene environment for swimming, picnicking, and enjoying the scenic coastline. The nearby Norwalk River also provides opportunities for kayaking and other water activities, making it a great spot for outdoor enthusiasts.

Another excellent choice is the downtown area, which boasts a vibrant atmosphere with a variety of shops, restaurants, and cafes. Staying in this part of Darien allows easy access to attractions such as the Darien Historical Society, where guests can learn about the town's rich history and heritage. The downtown area typically offers a good number of holiday rental properties, suiting different preferences and budgets, making it a convenient base for exploring the community.
How much does it cost to rent a holiday home in Darien?
Prices for holiday rentals in Darien vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Darien to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Darien holiday house rentals?
You can find great discounts on house rentals in Darien on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Darien?
For renting a beach house in Darien, Connecticut, the ideal locations include the scenic shores along Long Island Sound, particularly near the beaches of Pear Tree Point and Tokeneke. These areas offer charming beachfront properties that often feature amenities such as expansive decks for sunbathing, outdoor dining spaces, and private access to the beach, making them superb for families or groups looking to enjoy a coastal retreat.

In addition to the beautiful beaches, properties in the vicinity frequently come with modern kitchens, spacious living areas, and sometimes even access to community amenities like swimming pools and tennis courts. The neighbourhood also boasts proximity to local parks and nature reserves, providing opportunities for kayaking and outdoor exploration.
What is the most popular type of holiday rental accomodation in Darien?
In Darien, holiday houses are the most popular type of rental accommodation, with several options available throughout the town. These properties are typically located in residential neighbourhoods, providing a tranquil environment that is superb for families or groups. Most holiday houses come with multiple bedrooms, fully equipped kitchens, and spacious living areas, allowing guests to feel at home during their stay. Additionally, many include outdoor spaces such as gardens or patios, ideal for relaxing after exploring the nearby attractions, including the picturesque beaches and local parks.
Are there any family house rentals in Darien?
In Darien, Connecticut, there are several family-friendly house rentals available. This charming town offers a variety of spacious homes ideal for families, with many located close to local parks and recreational areas. Properties often come equipped with amenities such as fully stocked kitchens, ample living spaces for gatherings, and outdoor areas great for children to play.
Can I rent a holiday home with a pool or hot tub in Darien?
In Darien, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This charming coastal town offers a serene environment, great for a relaxing getaway. Many properties in Darien come with amenities such as private swimming pools, hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens for home-cooked meals.
Can I find long-stay holiday rentals in Darien?
A long-stay holiday rental in Darien is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Darien?
In Darien, Connecticut, there are several pet-friendly house rentals available, providing a comfortable stay for travellers with pets. Many of these properties are located in quiet residential areas, offering spacious living spaces and well-equipped kitchens, ideal for families or groups. Amenities may include private gardens, outdoor seating areas, and sometimes even pet-friendly features such as dog runs or easy access to nearby parks.
Are there any remote work holiday rentals in Darien?
In Darien, Connecticut, there are several holiday rentals that cater to remote workers. These properties typically offer amenities such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a conducive environment for productivity. Many of the rentals also feature additional comforts like spacious living areas and fully equipped kitchens, allowing for a pleasant work-life balance during your stay. The town itself is a charming coastal community, providing access to beautiful parks, local shops, and dining options, superb for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Darien holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Darien with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Darien?
In Darien, popular holiday rental amenities include essential kitchen appliances such as dishwashers and microwaves, making meal preparation convenient for travellers. Many rentals are equipped with cookware, dishware, and utensils, allowing guests to enjoy home-cooked meals in the comfort of their accommodation.
When is the best time to visit Darien for a holiday rental?
The best time to visit Darien for a holiday rental is during the peak season from May to July. This vibrant period attracts families and beachgoers eager to enjoy the warm summer weather, with temperatures typically ranging from the mid-teens to low 30s Celsius. The town's picturesque coastal charm shines through, making it superb for outdoor activities such as biking along scenic trails or relaxing on the sandy beaches.

July, in particular, stands out as the most popular month for travellers. The lively atmosphere is enhanced by various local events and festivals that celebrate the community's rich culture and history. With plenty of sunshine and opportunities for water sports, it's an excellent time for those looking to immerse themselves in the local lifestyle.

For those seeking a more budget-friendly experience, consider visiting in December. While it's a quieter time, the holiday season brings its own charm, with festive decorations and a magical ambiance. This is a wonderful opportunity to enjoy cosy winter walks and explore the town's unique shops.
How early should I book a Darien holiday rental?
Book your Darien holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Darien?
In Darien, visitors can enjoy a range of attractions that highlight the town's charm and natural beauty. The picturesque beaches along Long Island Sound, such as Pear Tree Point Beach and Weed Beach, are popular spots for sunbathing and swimming, offering scenic views and family-friendly facilities. Nature enthusiasts may also appreciate the nearby Goodwives River Park, which features walking trails and serene picnic areas.
Can I change or cancel my Darien home rental booking on Vrbo?
To find Darien holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Darien holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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