A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for New Canaan vacation rentals

Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (134 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is P7,977
P9,174 total
includes taxes & fees
Jul 5 - Jul 6
Stamford Suites
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, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is P11,124
P16,535 total
includes taxes & fees
Jul 27 - Jul 28
DUNE Fairfield Beach
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 P21,962
P25,256 total
includes taxes & fees
Jul 13 - Jul 14
Guesthouse at Norwalk Inn
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 P16,334
P29,541 total
includes taxes & fees
Jul 2 - Jul 3
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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 P27,529
P41,610 total
includes taxes & fees
Jul 9 - Jul 10
Luxury NYC Home with Free Parking for 12
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 P64,908
P101,807 total
includes taxes & fees
Jul 14 - Jul 15
Summer Pool Oasis Custom Bar Arcade Pool Table
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is P37,352
P64,366 total
includes taxes & fees
Jul 5 - Jul 6
Beechmont - Perfect for Family Retreat!
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is P58,116
P73,842 total
includes taxes & fees
Jul 4 - Jul 5
Prime Luxe 3-BR NYC - Free Parking
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 P61,175
P77,249 total
includes taxes & fees
Jul 8 - Jul 9
3BR Prime Luxury NY - Free Parking
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 P37,112
P51,587 total
includes taxes & fees
Aug 1 - Aug 2
Luxury NYC Home Game Room Free Parking
Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is P14,376
P45,184 total
includes taxes & fees
Jul 22 - Jul 23
3 Mi to Downtown: Spacious White Plains Home
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 P31,627
P46,699 total
includes taxes & fees
Jul 7 - Jul 8
4 Mi to Beach & Dtwn! Charming Fairfield Home
4 bedrooms, Internet

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is P53,691
P77,785 total
includes taxes & fees
Jul 12 - Jul 13
Stareway to Heaven in Fairfield
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"This is a clean hotel. Not perfect as my room did was a bit stale smelling, which seemed to come from the ac unit."
Kenneth 1-night trip
Posted 10 hours ago
Baymont by Wyndham White Plains - Elmsford

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 New Canaan Historical Society, whereas Old Stamford Road Bird Sanctuary and Mead Memorial Park 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.