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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for New Canaan holiday rentals

Classic Suite | 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, (84 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ฿5,730
฿8,544 total
includes taxes & fees
16 Apr - 17 Apr
DUNE Fairfield Beach
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
The price is ฿8,490
฿14,484 total
includes taxes & fees
14 Apr - 15 Apr
Luxury NYC Home Game Room Free Parking
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ฿28,591
฿44,093 total
includes taxes & fees
14 Apr - 15 Apr
Beechmont - Perfect for Family Retreat!
Villa | 5 bedrooms

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is ฿15,838
฿32,432 total
includes taxes & fees
14 Apr - 15 Apr
Westchester Summer Pool Pet Friendly Events Games
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 ฿11,501
฿13,226 total
includes taxes & fees
14 Apr - 15 Apr
Guesthouse at Norwalk Inn
Luxury House | Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is ฿9,611
฿15,766 total
includes taxes & fees
1 May - 2 May
Luxury 3BR Home Game Room Free Parking
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 ฿32,037
฿40,455 total
includes taxes & fees
14 Apr - 15 Apr
3BR Prime Luxury NY - Free Parking
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ฿9,611
฿15,478 total
includes taxes & fees
1 May - 2 May
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!
3.0 star property
Greenwich
The price is ฿2,755
฿9,816 total
includes taxes & fees
14 Apr - 15 Apr
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury House | Bathroom

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking
4.0 star property
White Plains
8.0 out of 10, Very good, (1 review)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
Luxury NY Home with Free Parking
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (107 reviews)
"Great location. "
United States
Christopher
The price is ฿4,767
฿5,482 total
includes taxes & fees
14 Apr - 15 Apr
Stamford Suites
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 ฿7,208
฿13,763 total
includes taxes & fees
14 Apr - 15 Apr
Luxury NYC Home with Free Parking for 12
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Clean everywhere and staff were so helpful and friendly! "
Amy 1-night trip
Posted 5 hours ago
Hampton Inn White Plains/Tarrytown

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:

  • 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.