Photo by (yu+ma)

New Canaan vacation rentals

We found 1,011 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in New Canaan that are perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Delight in the oceanfront landscape of New Canaan

Experience the unique character of New Canaan with a stay in a vacation home rental. This romantic city allures visitors with 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 attractions to see in the area? Venture out of your cozy vacation rental and experience everything that New Canaan has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Norwalk Maritime Aquarium (5.2 mi / 8.4 km)
  • Chelsea Piers (6.6 mi / 10.6 km)
  • Connecticut Golf Club (11.8 mi / 19 km)
  • Fairchild Wheeler Golf Course (13.8 mi / 22.3 km)
  • Rye Playland (15.6 mi / 25.1 km)
  • Beardsley Zoo (16.9 mi / 27.2 km)

Exploring the natural landscape of New Canaan

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, New Canaan is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Old Mill Beach (6.3 mi / 10.2 km)
  • 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)
  • Weir Farm National Historic Site (7.9 mi / 12.7 km)
  • Compo Beach (7.9 mi / 12.8 km)

Transportation options to and around New Canaan

Fly into Westchester County Airport (HPN), the closest airport, located 12.1 mi (19.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 15.6 mi (25.1 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in New Canaan?
The average price for a vacation home in New Canaan can vary depending on factors such as property type, length of stay and season. Whether you’re in search of a sprawling house with room for friends and family or a cozy condo for you and your other half, just enter your dates of travel to discover stays with exceptional value.
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 the cost of your beachside vacation rental. Enter your New Canaan travel dates to see your options on Vrbo. Can’t live without a private pool? Use the filters to choose the features and amenities you want.
Are there pet-friendly vacation rentals in New Canaan?
Pack a bone and a squeezy toy for your pup because New Canaan has eight properties that roll out the welcome mat to doggie guests. Let your furriest friend enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in New Canaan?
Add an extra element of fun to your vacation by staying in one of the five houses with a private pool in New Canaan. Use our search filter to find the kind of property you want on Vrbo, and then spend your days splishing and splashing in a swimming pool that’s for your use only.
What are popular rental amenities in New Canaan?
When it comes to rental amenities that guests are searching for in New Canaan, a fireplace, tennis and a sauna are the most popular. With Vrbo vacation rentals, there are choices to match your style and taste, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in New Canaan?
With five vacation rentals that can sleep 10 or more people in New Canaan, you won’t have to keep your invite list short. From extended family vacations to special events like weddings and birthday parties, Vrbo will help you find a large group rental that fits the occasion.
Are there vacation rentals in New Canaan that welcome kids?
With eight family-friendly vacation homes available in New Canaan, now is the perfect time to introduce the kiddos to the pleasures of travel. Click on our “Properties good for families” filter to find stays packed with amenities perfect for families on the move, such as kitchens, patios, entertainment areas and hot tubs.
What are the top attractions for families in New Canaan?
There are plenty of exciting things to see and do with the family in New Canaan, including:

  • Waveny Park
  • The Glass House
  • Silvermine Arts Center

Are there vacation rentals with WiFi in New Canaan?
Whether you want to stay in touch with world events, send some emails or surf social media, there are three vacation homes with WiFi in New Canaan. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in New Canaan?
Pick your dates and then use the filter tool to view vacation rentals with air conditioning in New Canaan on Vrbo. With eight air-conditioned properties available, you can enjoy a cool and comfy stay.
How old do you have to be to rent a vacation rental in New Canaan?
We advise checking with the New Canaan vacation rental you’re looking at on Vrbo as the age limit varies. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in New Canaan for?
The length of time you can rent a vacation rental in New Canaan varies according to the property. Just enter your chosen dates to see a list of options offering extended stays. With loads of amenities like air conditioning and kitchens, as well as some offering weekly or monthly discounts, you’re sure to discover the perfect place to call your home away from home in New Canaan.
Does Vrbo offer discounts for vacation homes in New Canaan?
Short stay or a much-needed extended escape, Vrbo has some exclusive deals and discounted options in New Canaan to match your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the ideal place to stay — without breaking the bank.

More Vacation Rentals ideas

People also search for