A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for New Canaan vacation rentals

Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (145 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is NT$4,340
NT$4,991 total
includes taxes & fees
Jul 29 - Jul 30
Stamford Suites
Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is NT$11,592
NT$13,331 total
includes taxes & fees
Jul 30 - Jul 31
Guesthouse at Norwalk Inn
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (103 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is NT$6,194
NT$9,098 total
includes taxes & fees
Aug 25 - Aug 26
DUNE Fairfield Beach
House (4 Bedrooms) | Interior

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$13,561
NT$21,047 total
includes taxes & fees
Aug 2 - Aug 3
4 Mi to Beach & Dtwn! Charming Fairfield Home
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NT$19,768
NT$34,065 total
includes taxes & fees
Jul 29 - Jul 30
Beechmont - Perfect for Family Retreat!
House | 4 bedrooms, high-speed internet

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is NT$27,792
NT$40,427 total
includes taxes & fees
Aug 26 - Aug 27
Stareway to Heaven in Fairfield
Luxury Apartment | In-room dining

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$29,060
NT$37,177 total
includes taxes & fees
Jul 29 - Jul 30
3BR Prime Luxury NY - Free Parking
Luxury Apartment | Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is NT$5,783
NT$11,425 total
includes taxes & fees
Aug 3 - Aug 4
Elegant Hideaway with Free Parking
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is NT$14,704
NT$21,629 total
includes taxes & fees
Jul 29 - Jul 30
Luxury NYC Home Game Room Free Parking
Luxury Villa, Garden View | Dining

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is NT$13,077
NT$20,344 total
includes taxes & fees
Aug 2 - Aug 3
Luxury NYC Home with Free Parking for 12
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NT$18,889
NT$25,849 total
includes taxes & fees
Aug 5 - Aug 6
Prime Luxe 3-BR NYC - Free Parking
Apartment (1 Bedroom) | Interior

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$5,489
NT$10,401 total
includes taxes & fees
Aug 3 - Aug 4
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
House | 5 bedrooms

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$32,244
NT$51,490 total
includes taxes & fees
Jul 29 - Jul 30
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

Trumbull Marriott Shelton

Trumbull Marriott Shelton

10/10 Excellent
"Staff was great"
Veronica 1-night trip
Posted 3 hours ago
Trumbull Marriott Shelton

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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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 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 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.