A highway surrounded by autumn foliage.

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Check prices for these dates

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

Our top choices for New Canaan holiday 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 ₹28,827
₹33,151 total
includes taxes & fees
1 Nov - 2 Nov
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 ₹15,946
₹18,338 total
includes taxes & fees
25 Oct - 26 Oct
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 ₹15,798
₹23,931 total
includes taxes & fees
22 Nov - 23 Nov
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 ₹31,080
₹47,703 total
includes taxes & fees
2 Nov - 3 Nov
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A breakfast buffet with pastries, fruits, and a coffee station.

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 ₹38,260
₹59,522 total
includes taxes & fees
25 Oct - 26 Oct
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 ₹46,762
₹67,560 total
includes taxes & fees
23 Oct - 24 Oct
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 ₹101,601
₹149,905 total
includes taxes & fees
26 Oct - 27 Oct
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 ₹16,919
₹33,427 total
includes taxes & fees
23 Oct - 24 Oct
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 ₹85,022
₹108,769 total
includes taxes & fees
23 Oct - 24 Oct
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 ₹80,771
₹104,034 total
includes taxes & fees
23 Oct - 24 Oct
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 ₹45,877
₹95,875 total
includes taxes & fees
3 Nov - 4 Nov
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 ₹57,532
₹87,425 total
includes taxes & fees
26 Oct - 27 Oct
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

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent
"The staff very helpful"
Tomasa 2-night trip
Posted less than an hour ago
Sleepy Hollow Hotel, a Dolce by Wyndham

Find out more about New Canaan

Holiday Rentals in New Canaan

Search for holiday rentals in New Canaan on Expedia.co.uk! 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 holiday rental in New Canaan?

Yes, there are holiday rentals in New Canaan close to Silvermine Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. New Canaan is known for its seafood restaurants.

How many holiday rentals will I find in New Canaan?

With 4 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in New Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Canaan. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.