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New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for New Canaan vacation rentals

Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Private kitchen
The Mansion Hotel-style

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is P4,994
P5,743 total
includes taxes & fees
Dec 30 - Dec 31
The Mansion Hotel-style
Lobby
Stamford Suites

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is P6,486
P7,459 total
includes taxes & fees
Dec 30 - Dec 31
Stamford Suites
Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is P16,390
P18,849 total
includes taxes & fees
Dec 30 - Dec 31
Guesthouse at Norwalk Inn
Free WiFi
Luxury 3BR Home Game Room Free Parking

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is P11,691
P22,124 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxury 3BR Home Game Room Free Parking
Private kitchen
Elegant Hideaway with Free Parking

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is P5,875
P15,473 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Elegant Hideaway with Free Parking
Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is P9,223
P18,665 total
includes taxes & fees
Dec 30 - Dec 31
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Free WiFi
Prime Luxe 3-BR NYC - Free Parking

Apartment in White Plains

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
The price is P11,691
P21,774 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Prime Luxe 3-BR NYC - Free Parking
5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Vacation Home in Ossining

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
The price is P20,841
P50,816 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Private kitchen
Luxury NY Home with Free Parking

Vacation Home in White Plains

Luxury NY Home with Free Parking
4.0 star property
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is P74,233
P90,720 total
includes taxes & fees
Dec 30 - Dec 31
Luxury NY Home with Free Parking
Dining
Luxury NYC Home with Free Parking for 12

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is P26,436
P39,959 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury NYC Home with Free Parking for 12
Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Luxury NYC Home Game Room Free Parking

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is P32,311
P45,709 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury NYC Home Game Room Free Parking
Front of property
Beechmont - Perfect for Family Retreat!

Vacation Home in North End

Beechmont - Perfect for Family Retreat!
5.0 star property
The price is P49,714
P77,733 total
includes taxes & fees
Dec 30 - Dec 31
Beechmont - Perfect for Family Retreat!
Reception
Global Luxury Suites White Plains

Apartment in White Plains

Global Luxury Suites White Plains
3.5 star property
6.8 out of 10, (34)
"Great location, spacious apartment and clean. The public areas like the hallway needed vacuuming but everything else was great."
United States
Jennifer
Global Luxury Suites White Plains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Canaan Hotel Reviews

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Everything was peaceful, clean and the attached restaurant was excellent. "
Henry 1-night trip
Posted 21 hours ago
Tarrytown House Estate

Find out more about New Canaan

Search for holiday rentals in New Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in New Canaan using one of the methods below:

  • View our selection of featured holiday rentals in New Canaan
  • Use the map to find apartments and other holiday homes in the New Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Canaan while they last

Look no further and take a look at our great range of rental properties in New Canaan!

Frequently asked questions

Can I find a vacation rental in New Canaan?

Yes, you can find vacation rentals in New Canaan near Goldenberry, or you can go with a secluded option if you want a relaxing stay. New Canaan is known for its seafood restaurants.

How many vacation rentals will I find in New Canaan?

With 6 Expedia vacation rentals, you're sure to find just the right place for your New Canaan stay.

What can I see and do in New Canaan?

Cultural attractions include The Glass House and Silvermine Arts Center, whereas Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Glass House Visitor's Center are other places to visit while you're in town.

What are vacation rentals like in New Canaan?

Vacation rentals are private accommodations you can book for a couple days or more in New Canaan. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.