New Canaan Holiday Rentals

Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for New Canaan holiday rentals

Property grounds

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$858
HK$1,206 total
includes taxes & fees
24 Feb - 25 Feb
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
1 bedroom, iron/ironing board, free WiFi, bed sheets

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is HK$938
HK$1,538 total
includes taxes & fees
22 Feb - 23 Feb
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$860
HK$2,147 total
includes taxes & fees
22 Feb - 23 Feb
Elegant Hideaway with Free Parking
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is HK$1,196
HK$2,531 total
includes taxes & fees
22 Feb - 23 Feb
Zen, Spacious & Comfy 2 bed, Lux beds
2 bedrooms, iron/ironing board, travel cot, WiFi

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is HK$827
HK$2,256 total
includes taxes & fees
25 Feb - 26 Feb
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$664
HK$1,145 total
includes taxes & fees
1 Mar - 2 Mar
Business or Weekend escape
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 HK$930
HK$2,228 total
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking
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 HK$1,149
HK$2,942 total
includes taxes & fees
21 Feb - 22 Feb
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,055
HK$2,176 total
includes taxes & fees
20 Feb - 21 Feb
Charming 1-bedroom apartment in Carmel with WiFi, AC
Smart TV, books

Family-Friendly Retreat With Trampoline & Grill

Family-Friendly Retreat With Trampoline & Grill
Locust Valley
The price is HK$1,090
HK$3,171 total
includes taxes & fees
20 Feb - 21 Feb
Family-Friendly Retreat With Trampoline & Grill
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, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Pool

Cozy In-law Garden Suite in Colonial Home

Cozy In-law Garden Suite in Colonial Home
Redding
The price is HK$1,000
HK$1,307 total
includes taxes & fees
20 Feb - 21 Feb
Cozy In-law Garden Suite in Colonial Home
Smart TV

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is HK$1,231
HK$2,324 total
includes taxes & fees
22 Feb - 23 Feb
Centric property close to all the great things in the city
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"The apartment overall is nice, and located in an area that is close to shops and dining. Listing photos are accurate, but as others have mentioned, this is not a "luxury" apartment. "
United States
Sheree G.
The price is HK$1,125
HK$2,458 total
includes taxes & fees
22 Feb - 23 Feb
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Terrace/patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is HK$971
HK$2,468 total
includes taxes & fees
25 Feb - 26 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
TV, fireplace, offices

Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
The price is HK$971
HK$2,640 total
includes taxes & fees
28 Feb - 1 Mar
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$1,555
HK$2,896 total
includes taxes & fees
1 Mar - 2 Mar
Prime Luxe 3-BR NYC - Free Parking
Fridge, microwave, oven, stovetop

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
6.8 out of 10, (3 reviews)
"Cozy get away"
United States
Anonymous traveller
The price is HK$1,171
HK$2,743 total
includes taxes & fees
20 Feb - 21 Feb
Modern 2 Bed in BlackRock
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 HK$4,298
HK$6,080 total
includes taxes & fees
20 Feb - 21 Feb
Luxury NYC Home Game Room Free Parking
Fridge, microwave, oven, stovetop

Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is HK$1,336
HK$2,010 total
includes taxes & fees
20 Feb - 21 Feb
Stylish Home and Cozy200
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

Hyatt House Shelton

Hyatt House Shelton

10/10 Excellent
"Room was very clean and staff were so so nice "
Jennifer 1-night trip
Posted 14 hours ago
Hyatt House Shelton

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!

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Frequently asked questions

Can I find a holiday rental in New Canaan?

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

What are some of the best holiday rentals that New Canaan has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of New Canaan is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in New Canaan?

With 6 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.