New Canaan holiday homes

We found 1,070 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in New Canaan to find one that's 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.

Holiday rentals with weekly discounts – New Canaan

Showing deals for:6 Nov - 13 Nov

Kitchen
View of back of house
Living room
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$14,817
for 7 nights, 1 home
NZ$2,117 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Property grounds
Interior
Private kitchen
Interior
Exceptional
(20 reviews)

Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

Brookfield

17% off
NZ$21,409
for 7 nights, 1 home
NZ$3,058 per night
includes taxes & fees
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Interior
Terrace/patio
Dining
Pool
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
NZ$17,329
for 7 nights, 1 home
NZ$2,476 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Room
Living area
Living area
Pool
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
NZ$31,484
for 7 nights, 1 home
NZ$4,498 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Room
Dining
Property grounds
Bar (on property)
Exceptional
(71 reviews)

Northport quaint restored Boathouse with sunset views!

Northport

8% off
NZ$5,159
for 7 nights, 1 cottage
NZ$737 per night
includes taxes & fees
Northport quaint restored Boathouse with sunset views!
Pool
Enjoy relaxing in the hot tub while watching TV!
Interior
Living area
Exceptional
(12 reviews)

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

Commack

7% off
NZ$12,385
for 7 nights, 1 home
NZ$1,769 per night
includes taxes & fees
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Exterior
Interior
Private kitchen
Property grounds
Exceptional
(30 reviews)

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury

8% off
NZ$13,689
for 7 nights, 1 home
NZ$1,956 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Exterior
relax and enjoy
Downstairs primary
Living area
Exceptional
(18 reviews)

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

Southbury

8% off
NZ$5,385
for 7 nights, 1 home
NZ$769 per night
includes taxes & fees
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury
main floor, king bed with bathroom, fireplace, slider opens to deck and hot tub.
Flat yard,
View from property
double fridge for extea space
Exceptional
(85 reviews)

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

New Fairfield

8% off
NZ$21,247
for 7 nights, 1 home
NZ$3,035 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Living area
Children’s area
Private kitchen
Interior
Exceptional
(49 reviews)

Quaint duplex with private yard. Walk to beach, dining, & shopping!

Greenwich

7% off
NZ$3,959
for 7 nights, 1 home
NZ$566 per night
includes taxes & fees
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Dining
Private kitchen
Exterior
Room
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
NZ$10,854
for 7 nights, 1 home
NZ$1,551 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Exterior
Marina
Outdoor dining
Interior
Exceptional
(14 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
NZ$2,229
for 7 nights, 1 apartment
NZ$318 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Property grounds
Exterior detail
Pool
Private kitchen
Exceptional
(38 reviews)

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

New Fairfield

8% off
NZ$4,238
for 7 nights, 1 apartment
NZ$605 per night
includes taxes & fees
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Room
Living area
Living area
Dining
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
NZ$2,141
for 7 nights, 1 apartment
NZ$306 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Interior
Interior
Room
Private kitchen
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
NZ$1,726
for 7 nights, 1 apartment
NZ$247 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Room
Property grounds
Living area
Living area
Exceptional
(7 reviews)

Spacious Lakeside Hideaway

Newtown

8% off
NZ$2,667
for 7 nights, 1 apartment
NZ$381 per night
includes taxes & fees
Spacious Lakeside Hideaway
Private kitchen
Interior
Dining
Interior
Exceptional
(9 reviews)

Luxurious 3BR/2BA Modern Haven Downtown Stamford

Stamford

8% off
NZ$6,349
for 7 nights, 1 apartment
NZ$907 per night
includes taxes & fees
Luxurious 3BR/2BA Modern Haven Downtown Stamford
  • 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, laundry, 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)
  • Hand & Stone Massage and Facial Spa (6.1 mi / 9.8 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)

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:

  • 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)
  • Cummings Park Beach (7.5 mi / 12.1 km)
  • West Beach (7.6 mi / 12.3 km)
  • Weir Farm National Historic Site (7.9 mi / 12.7 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 home accommodation in New Canaan?
Houses are the most popular type of holiday home in New Canaan, according to our data. Even if you have a different idea in mind, Bookabach 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 home in New Canaan?
A range of factors influence the price of a holiday home in New Canaan, like the time of year, length of stay and property type. Still, all Bookabach 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 home. Click on your New Canaan travel dates to view your options on Bookabach. 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 homes in New Canaan?
With eight holiday homes 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 homes and find the pawfect pad on Bookabach.
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 Bookabach. Ball games, gentle soak or noodle joust? Leisure time is up to you when your Bookabach holiday home boasts its own swimming pool.
What are popular home amenities in New Canaan?
A firepit, a swimming pool and nearby museums are rated the most popular home amenities in New Canaan. Whether you plan to travel by yourself, with your spouse or as a family group, Bookabach will help you find a holiday home that suits your style with all the features you're looking for.
Are there large group holiday homes 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 homes in New Canaan that welcome kids?
With eight family-friendly holiday homes 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 homes with WiFi in New Canaan?
New Canaan has two holiday homes 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 Bookabach homes make it a cinch to go online.
How can I find holiday homes 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 home in New Canaan?
The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Bookabach, so check the rules of your preferred New Canaan holiday home before booking your stay.
How long can I rent a holiday home in New Canaan for?
The length of time you can book a holiday home in New Canaan is down to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With loads of features such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in New Canaan.

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