New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for New Canaan vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is NT$5,230
NT$6,015 total
includes taxes & fees
Nov 8 - Nov 9
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NT$11,165
NT$12,840 total
includes taxes & fees
Dec 1 - Dec 2
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NT$5,844
NT$8,729 total
includes taxes & fees
Nov 22 - Nov 23
DUNE Fairfield Beach
A wooden gazebo with a lattice roof overlooking a forested area with a stream.

4. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is NT$10,808
NT$16,589 total
includes taxes & fees
Nov 8 - Nov 9
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A modern kitchen with a large island, wooden cabinets, and pendant lighting.

5. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is NT$30,590
NT$43,663 total
includes taxes & fees
Nov 24 - Nov 25
Stareway to Heaven in Fairfield
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

6. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NT$20,549
NT$35,129 total
includes taxes & fees
Nov 8 - Nov 9
Beechmont - Perfect for Family Retreat!
A breakfast buffet with pastries, fruits, and a coffee station.

7. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is NT$29,567
NT$37,825 total
includes taxes & fees
Nov 8 - Nov 9
3BR Prime Luxury NY - Free Parking
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

8. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is NT$20,007
NT$30,403 total
includes taxes & fees
Nov 8 - Nov 9
4 Mi to Beach & Dtwn! Charming Fairfield Home
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is NT$16,115
NT$33,521 total
includes taxes & fees
Nov 9 - Nov 10
Summer Pool Oasis Custom Bar Arcade Pool Table
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

A wooden interior with a reception desk, framed botanical prints, and a sign reading "The Water."
The Watershed

The Watershed

The Watershed
Cranbury

10/10 Excellent

Beautiful hotel! We would definitely stay again.
United States
Donna
Reviewed June 24, 2025
The Watershed

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:

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Frequently Asked Questions

Can I find a vacation rental in New Canaan?

Yes, you can find vacation rentals in New Canaan near Silvermine Arts Center, 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 4 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 John Rogers Studio and Museum, whereas God's Acre and Old Stamford Road Bird Sanctuary are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Silvermine Arts 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.