New Canaan holiday homes

We found 1,074 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:25 Dec - 1 Jan

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

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$15,277
for 7 nights, 1 home
NZ$2,182 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Family room by night with garage doors retracted.
Outdoor dining
Cozy library.
Private kitchen
Exceptional
(122 reviews)

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Danbury

7% off
NZ$7,384
for 7 nights, 1 home
NZ$1,055 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Fully stocked kitchen with stainless steel appliances and breakfast counter
Enjoy lounging after a long beach day on the sectional looking out at the water
Exterior
Open layout living
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

7% off
NZ$13,554
for 7 nights, 1 home
NZ$1,936 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Dining
Terrace/patio
Interior
Pool
Exceptional
(5 reviews)

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

Trumbull

8% off
NZ$17,867
for 7 nights, 1 home
NZ$2,552 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Living area
Living area
Room
Pool
Exceptional
(5 reviews)

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

Fairfield

8% off
NZ$37,673
for 7 nights, 1 home
NZ$5,382 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
double fridge for extea space
Flat yard,
main floor, king bed with bathroom, fireplace, slider opens to deck and hot tub.
Living area
Exceptional
(87 reviews)

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

New Fairfield

8% off
NZ$23,505
for 7 nights, 1 home
NZ$3,358 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Room
Private kitchen
Interior
Exterior
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
NZ$11,191
for 7 nights, 1 home
NZ$1,599 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Private kitchen
Living area
Pool
Dining
Exceptional
(24 reviews)

6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED

Carmel

8% off
NZ$16,309
for 7 nights, 1 home
NZ$2,330 per night
includes taxes & fees
6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
Children’s area
Children’s area
Private kitchen
Outdoor dining
Exceptional
(25 reviews)

Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.

Greenwich

8% off
NZ$5,770
for 7 nights, 1 home
NZ$824 per night
includes taxes & fees
Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.
Primary BR
Family room
Interior
Exterior
Exceptional
(22 reviews)

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Carmel

12% off
NZ$8,675
for 7 nights, 1 home
NZ$1,239 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Interior
Marina
Exterior
Living area
Wonderful
(16 reviews)

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

Stamford

7% off
NZ$2,586
for 7 nights, 1 apartment
NZ$369 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Living area
Private kitchen
Private kitchen
Interior
Exceptional
(17 reviews)

Downtown One Bedroom Suite Steps to Metro North

Harrison

16% off
NZ$3,273
for 7 nights, 1 apartment
NZ$468 per night
includes taxes & fees
Downtown One Bedroom Suite Steps to Metro North
Room
Living area
Bathroom
Interior
Exceptional
(37 reviews)

1 bedroom Cozy, comfy, super clean, great location and own entrance!!

Shelton

7% off
NZ$1,013
for 7 nights, 1 apartment
NZ$145 per night
includes taxes & fees
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Dining
Living area
Private kitchen
Room
Very good
(13 reviews)

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

Stamford

7% off
NZ$2,741
for 7 nights, 1 apartment
NZ$392 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$1,780
for 7 nights, 1 apartment
NZ$254 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

  • 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)
  • Chelsea Piers (6.6 mi / 10.6 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)
  • Hudson Hills Golf Course (17.3 mi / 27.9 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:

  • Sleepy Hollow Park (3.9 mi / 6.3 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)
  • Compo Beach (7.9 mi / 12.8 km)
  • Lucius Pond Ordway / Devil's Den Preserve (8.1 mi / 13 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 best area to stay in New Canaan when booking a holiday rental?
When considering a holiday rental in New Canaan, Connecticut, a popular area to stay is the charming downtown district. This vibrant neighbourhood is known for its picturesque streets and a delightful selection of boutique shops and cafes, making it an ideal spot for those who enjoy a lively yet relaxed atmosphere. You'll find a variety of properties available, ranging from charming historic homes to modern rentals, suiting different tastes and budgets.While you're in the area, don't miss the opportunity to visit the New Canaan Nature Centre, which offers beautiful walking trails and a chance to connect with nature. Additionally, the Philip Johnson Glass House is a must-see attraction, showcasing stunning architecture and providing insight into the design philosophy of one of America's most influential architects.
What is the most popular type of holiday rental accomodation in New Canaan?
In New Canaan, holiday houses are the most popular type of holiday rental, with around 12 available throughout the area. These homes are typically spacious and well-suited for families or groups, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Additionally, there are several apartments, cottages, and villas that offer alternative accommodation options. These rentals often provide a comfortable and homely atmosphere, allowing visitors to enjoy the charm of New Canaan while being close to local attractions and amenities.
Are there any family house rentals in New Canaan?
In New Canaan, Connecticut, there are several family-friendly house rentals available, providing ample options for those travelling with children. This charming town features spacious properties that often come equipped with generous living areas, fully stocked kitchens for family meals, and outdoor spaces for children to enjoy. Many homes also offer amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all.Visitors will appreciate the proximity to local parks, such as Waveny Park, which boasts playgrounds, walking trails, and picnic spots, great for family outings. Additionally, the town centre is home to a variety of shops and restaurants, allowing families to immerse themselves in the local culture while enjoying casual dining experiences.
Can I rent a holiday home with a pool or hot tub in New Canaan?
In New Canaan, there are several holiday homes available for rent that feature pools and hot tubs, providing a ideal setting for relaxation and enjoyment. This charming town in Connecticut offers a mix of beautiful residential neighbourhoods, where travellers can find properties with various amenities. Many rentals come equipped with private swimming pools, hot tubs, outdoor seating areas, and fully stocked kitchens, making them ideal for families or groups seeking a comfortable getaway.
Are there pet-friendly house rentals in New Canaan?
In New Canaan, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. Many of these properties come equipped with modern amenities such as spacious kitchens, comfortable living areas, and private outdoor spaces for your furry companions to enjoy.The area is known for its picturesque surroundings, including parks and nature trails that are superb for walks with pets. For instance, Waveny Park, located nearby, offers expansive green spaces, walking paths, and even a dog park, ensuring plenty of opportunities for outdoor activities. Additionally, the charming downtown area features pet-friendly cafes and shops, ideal for both you and your pet.
Are there any remote work holiday rentals in New Canaan?
In New Canaan, Connecticut, there are several options for remote work holiday rentals, with around 21 properties available to suit various needs. This charming town offers a tranquil setting for remote workers, and many rentals come equipped with essential amenities such as high-speed internet, free Wi-Fi, and dedicated workspaces including desks and comfortable chairs.The area is known for its picturesque surroundings and access to local parks, making it an ideal escape for those looking to balance work and leisure. Nearby, you'll find points of interest like the New Canaan Nature Centre and the charming downtown area, which features lovely shops and restaurants. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in New Canaan?
In New Canaan, popular rental amenities include fully equipped kitchens, which are essential for those who prefer to prepare their own meals. Many properties also feature blenders, ideal for making smoothies or other beverages. Outdoor spaces like decks or patios are common, providing a pleasant area for relaxation and enjoying the fresh air. Additionally, many rentals come with fireplaces, enhancing comfort during cooler months. For travellers with pets, it's worth noting that several holiday rentals in the area permit pets, allowing guests to bring their furry companions along on their stay.
When is the best time to visit New Canaan for a holiday rental?
April marks the beginning of the peak travel season in New Canaan, making it an ideal time to consider booking a holiday rental. As spring unfolds, visitors are drawn to the area's lush landscapes and blooming gardens, great for outdoor activities and leisurely strolls through the town's charming streets. Between April and June, you'll find a vibrant setting, with opportunities for sightseeing and enjoying the local art scene.During April, temperatures typically range from 5 to 15 degrees Celsius, providing a comfortable climate for exploring the beautiful parks and historic sites that New Canaan has to offer. The popular Waveny Park, with its expansive greenery and picturesque views, is especially inviting during this season, making it a fantastic spot for picnics and outdoor gatherings.For those seeking a more budget-friendly option, consider visiting in December. While this month may be quieter, it offers a unique charm as the town lights up for the holiday season, featuring festive decorations and local events that create a warm, welcoming atmosphere.Ultimately, your choice will depend on whether you prefer the lively spring vibe with blooming nature and community activities or the peaceful charm of wintertime in New Canaan.
What are the top attractions in New Canaan?
In New Canaan, visitors can enjoy a variety of attractions that highlight the town's charm and natural beauty. The Waveny Park is a popular destination, featuring expansive lawns, beautiful gardens, and the iconic Waveny House, which often hosts community events. This area is superb for leisurely walks and picnics.Another popular attraction is the New Canaan Nature Centre, where families can explore trails, visit animal exhibits, and engage in educational programs. The centre's serene environment makes it a great spot for outdoor activities and enjoying the local flora and fauna.For those interested in art and culture, the Silvermine Arts Centre offers a range of exhibitions and classes, celebrating local artists and the creative community. The nearby Silvermine Historic District is also worth exploring, with its charming architecture and artistic heritage.
Are all fees included in the New Canaan holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any New Canaan holiday homes with parking?
Bookabach offers a wide selection of holiday homes in New Canaan with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for New Canaan holiday homes?
You can find great discounts on holiday homes in New Canaan on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my New Canaan holiday home booking on Bookabach?
To find New Canaan holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in New Canaan?
A long-stay holiday home in New Canaan is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a New Canaan holiday home?
Book your New Canaan holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in New Canaan?
Prices for holiday homes in New Canaan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in New Canaan to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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