A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for New Canaan vacation rentals

Exterior

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (178 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NT$5,074
NT$5,835 total
includes taxes & fees
Sep 20 - Sep 21
Stamford Suites
Standard Room, 1 King Bed, Main Building | Property entrance

2. 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$11,418
NT$13,131 total
includes taxes & fees
Sep 21 - Sep 22
Guesthouse at Norwalk Inn
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NT$5,655
NT$8,447 total
includes taxes & fees
Sep 28 - Sep 29
DUNE Fairfield Beach
House (4 Bedrooms) | Interior

4. 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$14,504
NT$23,838 total
includes taxes & fees
Sep 21 - Sep 22
4 Mi to Beach & Dtwn! Charming Fairfield Home
Front of property

5. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NT$31,751
NT$47,645 total
includes taxes & fees
Sep 20 - Sep 21
Beechmont - Perfect for Family Retreat!
Villa, Garden View | Living area

6. 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$15,744
NT$22,746 total
includes taxes & fees
Sep 28 - Sep 29
Luxury NYC Home Game Room Free Parking
Luxury Villa, Garden View | Dining

7. 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$12,881
NT$20,040 total
includes taxes & fees
Sep 24 - Sep 25
Luxury NYC Home with Free Parking for 12
Dining

8. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NT$17,175
NT$23,868 total
includes taxes & fees
Sep 18 - Sep 19
Prime Luxe 3-BR NYC - Free Parking
Luxury Apartment | In-room dining

9. 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$28,625
NT$36,621 total
includes taxes & fees
Sep 18 - Sep 19
3BR Prime Luxury NY - Free Parking
Luxury Apartment | Private kitchen

10. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is NT$5,696
NT$11,254 total
includes taxes & fees
Sep 22 - Sep 23
Elegant Hideaway with Free Parking
House | 5 bedrooms

11. 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$20,958
NT$39,226 total
includes taxes & fees
Sep 21 - Sep 22
Summer Pool Oasis Custom Bar Arcade Pool Table
Apartment (1 Bedroom) | Interior

12. 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$10,464
NT$16,061 total
includes taxes & fees
Sep 30 - Oct 1
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
House (5 Bedrooms) | Interior

13. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
The price is NT$8,683
NT$25,921 total
includes taxes & fees
Sep 20 - Sep 21
Nyc-area Escape Near River, Trails & Mta!
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
"Beautiful property and grounds! Very friendly staff."
Mark 1-night trip
Posted less than an hour 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:

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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 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.