A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for New Canaan vacation rentals

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

1. 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$11,670
NT$13,421 total
includes taxes & fees
Oct 22 - Oct 23
Guesthouse at Norwalk Inn
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (197 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NT$5,331
NT$6,131 total
includes taxes & fees
Oct 22 - Oct 23
Stamford Suites
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, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NT$5,768
NT$8,616 total
includes taxes & fees
Oct 29 - Oct 30
DUNE Fairfield Beach
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

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$10,695
NT$16,415 total
includes taxes & fees
Oct 22 - Oct 23
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

5. 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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
The price is NT$13,166
NT$20,482 total
includes taxes & fees
Oct 22 - Oct 23
Luxury NYC Home with Free Parking for 12
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

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$16,091
NT$23,248 total
includes taxes & fees
Oct 22 - Oct 23
Luxury NYC Home Game Room Free Parking
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

7. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NT$34,962
NT$51,585 total
includes taxes & fees
Nov 3 - Nov 4
Beechmont - Perfect for Family Retreat!
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

8. 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$5,822
NT$11,503 total
includes taxes & fees
Oct 22 - Oct 23
Elegant Hideaway with Free Parking
A breakfast buffet with pastries, fruits, and a coffee station.

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$29,257
NT$37,429 total
includes taxes & fees
Oct 22 - Oct 23
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

10. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NT$27,794
NT$35,800 total
includes taxes & fees
Oct 22 - Oct 23
Prime Luxe 3-BR NYC - Free Parking
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.

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$15,850
NT$33,123 total
includes taxes & fees
Nov 3 - Nov 4
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

12. 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$19,797
NT$30,084 total
includes taxes & fees
Oct 22 - Oct 23
4 Mi to Beach & Dtwn! Charming Fairfield Home
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

13. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
Snow Days & City Escapes: Spacious Ossining Home
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

Amsterdam Hotel

Amsterdam Hotel

8/10 Good
"The Amsterdam was an excellent value for money. We stayed one night to attend a concert in nearby Norwalk so only used the room for sleeping. Although the decor is dated, the rooms and hallways were extremely clean and the front desk, cleaners, and other staff were friendly and helpful. The hotel felt safe and secure and the free on-site parking and nearby food selections made the location accessible. Definitely recommended for short stays."
J Duffy 1-night trip
Posted 3 hours ago
Amsterdam Hotel

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 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.