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New Canaan holiday lettings

We found 929 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 7 homes and other holiday rentals in New Canaan that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Delight in the oceanfront landscape of New Canaan

Learn about the unique charm of New Canaan with a stay in a holiday home rental. This romantic city attracts visitors thanks to its coral reefs and seafood restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around New Canaan

Are you looking for things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes New Canaan a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (5.2 mi / 8.4 km)
  • Chelsea Piers (6.6 mi / 10.6 km)
  • Country Club of Fairfield (11.6 mi / 18.7 km)
  • Rye Playland (15.6 mi / 25.1 km)
  • Beardsley Zoo (16.9 mi / 27.2 km)
  • Bayville Adventure Park (17.1 mi / 27.6 km)

Exploring the natural landscape of New Canaan

Whether you're looking for exciting outdoor activities or just want to take in the scenery, New Canaan is a great spot to appreciate mother nature. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Calf Pasture Beach (6.8 mi / 10.9 km)
  • Cove Island Park (6.9 mi / 11.1 km)
  • West Beach (7.6 mi / 12.3 km)
  • Compo Beach (7.9 mi / 12.8 km)
  • Greenwich Point Park (10.9 mi / 17.5 km)
  • Fairfield Beach (12.6 mi / 20.3 km)

Transport options to and around New Canaan

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 12.1 mi (19.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 15.6 mi (25.1 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in New Canaan?

Houses are the most popular type of holiday rental in New Canaan, according to our data. Even if you have a different idea in mind, Vrbo has properties in a variety of shapes and sizes. Compare our options to find your perfect fit.

How much does it cost to rent a holiday rental in New Canaan?

A range of factors influence the price of a holiday rental in New Canaan, like the time of year, length of stay and property type. Still, all Vrbo homes have one thing in common — excellent value. Just enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in New Canaan?

When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday rental. Click on your New Canaan travel dates to view your options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you want in your beach house.

Are there pet-friendly holiday rentals in New Canaan?

With eight holiday rentals that welcome four-legged guests, your furry companion can join you on your New Canaan getaway. Use our filter tool to search our pet-friendly holiday rentals and find the pawfect pad on Vrbo.

Can I rent a house with a pool in New Canaan?

Tick the "pool" box in our filter tool and you'll find five houses with private pools in New Canaan on Vrbo. Ball games, gentle soak or noodle joust? Leisure time is up to you when your Vrbo holiday home boasts its own swimming pool.

What are popular rental amenities in New Canaan?

A firepit, a swimming pool and nearby museums are rated the most popular rental amenities in New Canaan. Whether you plan to travel by yourself, with your spouse or as a family group, Vrbo will help you find a holiday home that suits your style with all the features you're looking for.

Are there large group holiday rentals in New Canaan?

Take your pick of two holiday properties in New Canaan that can sleep 10 or more people. Whether you're organising a get-together with extended family or a celebration like a birthday, there's plenty of space to get your loved ones together under the same roof.

Are there holiday rentals in New Canaan that welcome kids?

With eight family-friendly holiday rentals to select from in New Canaan, there's never been a better time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter box to browse stays loaded with amenities perfect for holidaying families, such as multiple bedrooms, swimming pools, hot tubs and entertainment areas.

What are the top attractions for families in New Canaan?

There's a ton of amazing things to see and do with the family in New Canaan, including:

  • Compo Beach
  • Norwalk Maritime Aquarium
  • The Maritime Aquarium

Are there holiday rentals with WiFi in New Canaan?

New Canaan has two holiday rentals with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Vrbo homes make it a cinch to go online.

How can I find holiday rentals with air conditioning in New Canaan?

There are eight holiday homes with air conditioning in New Canaan providing that cooling breeze and extra bit of comfort. Enter your chosen travel dates and then use our filters to look for properties with air conditioning.

How old do you have to be to rent a holiday rental in New Canaan?

The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Vrbo, so check the rules of your preferred New Canaan holiday home before booking your stay.

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