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New Canaan Luxury Rentals

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Why Choose Rent By Owner for your New Canaan Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Popular Areas for New Canaan Vacation Rentals

Where are the best neighborhoods to stay in New Canaan?

When planning your stay in New Canaan, Connecticut, exploring the different neighborhoods can help you find the perfect setting for your getaway. Each area offers its own unique charm and character, allowing you to choose a location that complements your vacation style. Whether you're seeking a peaceful residential community or a lively neighborhood with convenient access to local amenities, you'll find options that suit your preferences. Discover the variety of neighborhoods in New Canaan to ensure your vacation rental provides both comfort and convenience during your visit to this picturesque part of Connecticut.

North Stamford

This area offers a peaceful setting with convenient access to natural beauty and local amenities, making it an ideal choice for your stay in the region. You’ll find that North Stamford provides a perfect balance of tranquility and accessibility for exploring nearby attractions.

View 187+ Rentals in North Stamford

Best Times to Visit New Canaan

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can enhance your experience, so consider the seasonal climate and local events to choose the best time for your stay here in New Canaan, Connecticut.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the area comes alive with lush greenery and blooming flowers, making it an ideal period for exploring outdoor spaces and enjoying pleasant weather.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September to October)

This period offers mild temperatures and beautiful fall foliage, creating a picturesque setting perfect for outdoor activities and scenic drives around here.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

The colder months see fewer visitors, providing a peaceful atmosphere ideal for cozy indoor stays and off-season exploration of the quieter parts of the region.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Early Spring (March to April)

Before the full bloom begins, the early spring offers lower occupancy, allowing you to enjoy the tranquil environment and explore at a relaxed pace here.

Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F

Weekly Weather Forecast for New Canaan

How to Book Your New Canaan 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 New Canaan

More Top-Rated Vacation Rentals in New Canaan 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 a private outdoor patio or deck perfect for relaxing or dining al fresco amidst the region’s scenic surroundings.
  • Take advantage of lush, landscaped gardens that enhance the natural beauty of your stay here.
  • Make use of a spacious yard or lawn ideal for outdoor activities and family gatherings.
  • Benefit from access to a swimming pool for refreshing dips during warmer months in this destination.
  • Utilize outdoor grilling facilities to host barbecues and enjoy meals under the open sky.
  • Experience the tranquility of a fire pit area, perfect for evening gatherings and storytelling.
  • Explore nearby walking trails or sprawling grounds that showcase the region’s charming landscape.

Top Attractions Around New Canaan

What attractions are nearby?

Within this charming area, you can enjoy a variety of outdoor activities, explore scenic parks, and visit cultural attractions that highlight the region's natural beauty and community spirit.

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Family Activities

  • Waveny Park: Enjoy a family picnic, explore scenic trails, and visit the historic Waveny House within this expansive public park.
  • New Canaan Nature Center: Discover wildlife exhibits, participate in educational programs, and stroll through the beautifully maintained nature trails.
  • Carriage Barn Arts Center: Engage in family-friendly art workshops and explore local art exhibitions in this cultural hub of the area.
  • Silvermine Arts Center: Experience creative activities and interactive exhibits designed to inspire children and bring families together here in the region.
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Adult Activities

  • Exploring the New Canaan Historical Society: Dive into local history and learn about the area's rich heritage through engaging exhibits and preserved landmarks.
  • Walking the Scenic Nature Trails: Enjoy peaceful strolls along well-maintained trails that showcase the natural beauty of this destination’s parks and outdoor spaces.
  • Visiting Waveny Park and Mansion: Spend your leisure time exploring the expansive parklands and touring the historic mansion that offers picturesque views and relaxing spots.
  • Shopping at Unique Boutiques and Art Galleries: Discover distinctive stores and galleries in the region, perfect for finding one-of-a-kind souvenirs or experiencing local artistry.

Other Places to Stay in New Canaan, CT

Fairfield County Primary Care
Fairfield County Primary Care Vacation Rentals
The Glass House
The Glass House Vacation Rentals
Goldenberry
Goldenberry Vacation Rentals
Silvermine Arts Center
Silvermine Arts Center Vacation Rentals
Steward House at Silver Hill Hospital
Steward House at Silver Hill Hospital Vacation Rentals
Waveny Park
Waveny Park Vacation Rentals
More Places to Stay Near New Canaan

New Canaan Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local attractions: Take time to visit the area's charming spots to truly immerse yourself in the character of this destination.
  • Plan outdoor activities: Make the most of the region's scenic parks and trails by scheduling outdoor adventures during your stay.
  • Discover culinary delights: Indulge in the local cuisine by exploring nearby cafes and restaurants for genuine regional flavors.
  • Connect with the community: Attend local events or markets to experience the welcoming atmosphere of the area firsthand.

Transportation Options

  • Metro-North Railroad: You can easily access this region via the Metro-North Railroad, which offers convenient train services connecting to nearby cities and major transportation hubs.
  • Bus Services: Local bus routes provide affordable and reliable transportation throughout the area, making it simple to explore without a car.
  • Taxi and Rideshare Services: Taxis and rideshare options are readily available for flexible travel around here, ensuring comfortable trips within the region.
  • Personal Vehicle Rentals: Renting a car is a popular choice for visitors who want the freedom to explore the area's attractions at their own pace.

Local Customs Options

  • Traditional New England Hospitality: Locals here take pride in their friendly and welcoming demeanor, making your stay in this charming area feel like visiting family.
  • Seasonal Celebrations: Participating in seasonal events such as fall festivals and holiday parades offers a glimpse into the community spirit that defines the region.
  • Local Dining Etiquette: Embracing the appreciation for farm-to-table cuisine reflects the area's commitment to fresh, local ingredients often enjoyed during your visit.
  • Preservation of Architectural Heritage: Respect for historic homes and buildings is evident, highlighting the community’s dedication to maintaining its timeless New England charm.

Frequently Asked Questions About New Canaan?

1. What are the top vacation rentals in New Canaan?

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

2. How many vacation rentals have private pools in New Canaan?

There are 13 vacation rentals with private pools near New Canaan. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in New Canaan are best for families?

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

4. How many Rentbyowner vacation rentals are available in New Canaan?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 146 in the New Canaan 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 New Canaan. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property owner. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with canceling your reservation.

6. How do I find out if a vacation rental allows pets?

Pet policies are listed on each property’s page. Be sure to read the pet policy information carefully or reach out to the host to confirm if bringing your pet is permitted during your stay.

7. Are there specific check-in and check-out times I need to be aware of?

Check-in and check-out times are specified in the property listing. It’s recommended to verify these times before confirming your booking or contacting the owner for any flexibility.

8. What amenities are typically included in a vacation rental here?

Amenities vary between properties, but common features include Wi-Fi, parking, fully equipped kitchens, and laundry facilities. For exact amenities, please review the individual listing details or inquire with the property owner.

9. How can I ensure my booking is secure and reliable?

Booking through reputable platforms ensures secure transactions and verified listings. Always read reviews, confirm the property details, and communicate directly with the owner for any questions before completing your reservation.