New Canaan Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for New Canaan holiday rentals

Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is S$1,759
includes taxes & fees
25 May - 26 May
Beechmont - Perfect for Family Retreat!
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (89 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is S$337
includes taxes & fees
26 May - 27 May
DUNE Fairfield Beach
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is S$1,542
includes taxes & fees
23 May - 24 May
Prime Luxe 3-BR NYC - Free Parking
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 S$745
includes taxes & fees
25 May - 26 May
4 Mi to Beach & Dtwn! Charming Fairfield Home
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 S$1,879
includes taxes & fees
28 May - 29 May
Summer Pool Oasis Custom Bar Arcade Pool Table
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 S$1,613
includes taxes & fees
23 May - 24 May
3BR Prime Luxury NY - Free Parking
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 S$517
includes taxes & fees
25 May - 26 May
Guesthouse at Norwalk Inn
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 S$994
includes taxes & fees
23 May - 24 May
Luxury NYC Home Game Room Free Parking
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (118 reviews)
"I stay there because it's fully equipped to cook and parking is excellent."
United States
fatima
The price is S$209
includes taxes & fees
8 Jun - 9 Jun
Stamford Suites
Hypo-allergenic bedding, desk, laptop workspace, iron/ironing board

Global Luxury Suites White Plains

Global Luxury Suites White Plains
3.5 star property
White Plains
6.8 out of 10, (43 reviews)
"Please stay away from this horrible place!!! I have travelled all over the world but never dealt with such terrible company and their property. "
United States
Katerine
The price is S$422
includes taxes & fees
26 May - 27 May
Global Luxury Suites White Plains
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 S$869
includes taxes & fees
23 May - 24 May
Luxury NYC Home with Free Parking for 12
Interior

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is S$562
includes taxes & fees
25 May - 26 May
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
3 Mi to Downtown: Spacious White Plains Home
Interior

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
Ossining Vacation Rental 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

East Norwich Inn

East Norwich Inn

10/10 Excellent
"Loved everything. Wish we had a microwave."
Gwen 7-night trip
Posted 11 hours ago
East Norwich Inn

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 Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and New Canaan Town Hall 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.