Discover Your Perfect Darien Vacation Homes

Darien Luxury Rentals

See More Darien Luxury Vacation Rentals
Find More Darien Villas, Resorts, & Rentals on BedroomVillas

Darien Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Darien on PetFriendly.io

Darien Large Vacation Homes

9.2 (12 Reviews)
House
Hollow Spring Retreat
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
View Availability
See More Family Vacation Rentals in Darien on FVR

Why Choose Rent By Owner for your Darien Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Darien Vacation Rentals

Where are the best neighborhoods to stay in Darien?

When planning your stay in Darien, Connecticut, selecting the right neighborhood can significantly enhance your visit. This charming area offers a variety of neighborhoods that cater to different preferences, whether you're seeking quiet residential streets or convenient access to local amenities. Each neighborhood provides a unique atmosphere, allowing you to find a comfortable and memorable base for exploring the beauty and tranquility of Darien. With trusted vacation rentals available throughout these neighborhoods, you’ll enjoy a seamless booking experience tailored to your needs, ensuring a relaxing and enjoyable trip.

Cove - East Side - Shippan

This area offers a peaceful retreat with scenic views and easy access to local amenities, making it an ideal choice for those seeking comfort and convenience. When staying here, you'll enjoy the tranquil ambiance while being close to key attractions in the region.

View 39+ Rentals in Cove - East Side - Shippan

Best Times to Visit Darien

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider planning your vacation during the ideal seasons when the weather and local events in this destination align to enhance your experience with the region’s charming atmosphere.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you'll enjoy warm weather ideal for outdoor activities and exploring the region's scenic beauty, making it a popular time to book vacation rentals here.

Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
autumn
Early Fall (September to October)

This season offers mild temperatures and vibrant fall foliage, creating an appealing atmosphere for visitors seeking a relaxing getaway in this destination.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

image
Winter (December to February)

The colder months see fewer visitors, providing a tranquil experience when you prefer quiet vacation rentals in the area.

Average Temperature Daytime: 35-45°F - Nighttime: 25-35°F
image
Late Fall to Early Winter (November)

As the region transitions into winter, the reduced crowd levels offer a peaceful environment for those seeking a more secluded retreat.

Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F

Weekly Weather Forecast for Darien

How to Book Your Darien Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Darien

More Top-Rated Vacation Rentals in Darien Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining spaces perfect for savoring meals al fresco during your stay in this charming region.
  • Relax by private pools or hot tubs available at select properties, ideal for unwinding after exploring nearby attractions.
  • Take advantage of well-maintained gardens and landscaped yards that enhance the outdoor ambiance of your rental.
  • Make the most of spacious patios and decks designed for entertaining or simply soaking up the scenic surroundings.
  • Utilize outdoor grilling areas to host barbecues and gather with friends or family in a cozy setting.
  • Explore well-equipped outdoor fire pits, providing warmth and ambiance on cooler evenings.
  • Access to nearby parks and green spaces where you can enjoy outdoor activities in the area.

Top Attractions Around Darien

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and scenic explorations just moments from your vacation rental, making it easy to experience the natural beauty and tranquil atmosphere that define the region.

image
image

Family Activities

  • Darien Nature Center: Explore this family-friendly spot to enjoy interactive exhibits and outdoor trails that showcase the region's natural beauty.
  • Weed Beach and Playground: Spend a relaxing day at the beach with your loved ones, where you can swim, build sandcastles, or enjoy the scenic shoreline views.
  • Darien Historical Society Museum: Discover the area's rich history through engaging exhibits and interactive displays perfect for curious minds of all ages.
  • Merritt Parkway Scenic Drive: Take a leisurely drive along this historic route, offering stunning views and photo opportunities that highlight the region’s charming landscape.
image

Adult Activities

  • Kayaking and Paddleboarding: Explore the calm waters and scenic coastline through kayaking or paddleboarding, immersing yourself in the natural beauty of this coastal area.
  • Visit the Darien Nature Center: Engage with local wildlife and enjoy educational exhibits at the nature center, perfect for connecting with the region’s outdoor environment.
  • Golfing at Darien Golf Course: Tee off at a well-maintained course that offers a relaxing day on the links amidst picturesque surroundings.
  • Shopping and Dining in Downtown Darien: Stroll through the charming downtown area to discover boutique shops and dine at renowned eateries, experiencing the culinary scene here.

Other Places to Stay in Darien, CT

McGuane Field
McGuane Field Vacation Rentals
Sleepy Hollow Park
Sleepy Hollow Park Vacation Rentals
Sapelo Island Visitors Center
Sapelo Island Visitors Center Vacation Rentals
More Places to Stay Near Darien

Darien Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Take advantage of the region's scenic shoreline by visiting nearby beaches for relaxing days in the sun and picturesque sunsets.
  • Discover Waterfront Dining: Savor fresh seafood and regional flavors at waterfront restaurants that highlight the area's culinary charm.
  • Visit Nature Trails: Enjoy outdoor activities by exploring local parks and nature trails to experience the natural beauty here firsthand.
  • Plan Cultural Outings: Immerse yourself in regional arts and community events that showcase the area's rich cultural heritage.

Transportation Options

  • Metro-North Railroad: This regional rail service offers convenient train connections from Darien to New York City and other nearby destinations, making it easy to explore the broader region.
  • Connecticut Transit Bus Service: Local bus routes provide affordable transportation options across the area, connecting you effortlessly to shopping centers, schools, and parks.
  • Driving Your Vehicle: Renting a car is an excellent way to explore at your own pace, with well-maintained roads leading to local attractions and neighboring towns.
  • Taxis and Ride-Sharing Services: Taxis and popular ride-sharing apps offer flexible, on-demand transportation around this destination, ideal for quick trips or when convenience matters most.

Local Customs Options

  • Community Events: Engaging in local community events allows you to experience the region's warm hospitality and traditions firsthand during your stay.
  • Dining Etiquette: Respect for seasonal seafood dishes and family-style dining is a cherished custom that reflects the area's culinary culture.
  • Celebration of Holidays: Participating in regional holiday celebrations, like Memorial Day and Fourth of July, offers insight into the area's patriotic spirit.
  • Recreational Traditions: Embracing the outdoor recreational customs, such as boating and coastal walks, helps you connect with the natural beauty of this destination.

Frequently Asked Questions About Darien?

1. What are the top vacation rentals in Darien?

There are a lot of options in Darien. If you plan on staying in the Darien area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Darien:

2. Which vacation homes in Darien are best for families?

If you are looking for a family-friendly vacation home in Darien, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Darien:

3. How many Rentbyowner vacation rentals are available in Darien?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 136 in the Darien area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Darien. 

4. What is the cancellation policy for vacation rentals in Darien, Connecticut?

Cancellation policies vary by property. You should review the specific listing details or contact the host directly to understand the applicable cancellation terms and possible refunds.

5. How do I confirm my reservation and what are the payment options?

Bookings are confirmed once you complete the payment process outlined on the listing. Payment methods typically include credit cards and other secure online options specified by the property owner.

6. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or taxes may apply. These will be clearly listed during your booking process, but it’s best to review the full fee details before confirming your reservation.

7. What amenities can I expect in a Darien vacation rental during my stay?

Amenities vary per property but commonly include essentials like Wi-Fi, parking, and fully equipped kitchens. Specific amenities are detailed in each listing, so reviewing them will help ensure the property meets your needs.

8. How do I find available dates and book a vacation rental in this destination?

You can check availability by selecting your preferred travel dates on the listing page. Once you choose a suitable property, follow the booking steps to reserve your stay securely online.