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New Canaan Vacation Rentals

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for New Canaan vacation rentals

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Stamford Suites

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (78)
"It was great"
United States
Natalie
$120 nightly
The price is $138
Dec 21 - Dec 22
Total with taxes and fees
Stamford Suites
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$221 nightly
The price is $254
Jan 5 - Jan 6, 2026
Total with taxes and fees
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Norwalk

Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very Good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$243 nightly
The price is $280
Dec 18 - Dec 19
Total with taxes and fees
Guesthouse at Norwalk Inn
Reception
Global Luxury Suites White Plains

Apartment in White Plains

Global Luxury Suites White Plains
3.5 star property
6.8 out of 10, (33)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Lounge
Luxury Apartments by Hyatus at The Asher

Aparthotel in Downtown Stamford

Luxury Apartments by Hyatus at The Asher
4.5 star property
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Vacation Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$228 nightly
The price is $258
Dec 15 - Dec 16
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Pool
Business or Weekend escape

Vacation Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
Jan 1 - Jan 2, 2026
Total with taxes and fees
Business or Weekend escape
Smart TV
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Apartment in Scarsdale

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
9.2 out of 10, Wonderful, (5)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
United States
Annette D.
$282 nightly
The price is $323
Jan 4 - Jan 5, 2026
Total with taxes and fees
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
Front of property
Beechmont - Perfect for Family Retreat!

Vacation Home in North End

Beechmont - Perfect for Family Retreat!
5.0 star property
$1,151 nightly
The price is $1,323
Dec 12 - Dec 13
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Outdoor dining
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven

Cottage in Croton-on-Hudson

Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven
Outdoor spa tub
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City

Cottage in Greenwich

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
3.0 star property
$875 nightly
The price is $991
Dec 11 - Dec 12
Total with taxes and fees
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Luxury House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Luxury NY Home with Free Parking

Vacation Home in White Plains

Luxury NY Home with Free Parking
4.0 star property
8.0 out of 10, Very Good, (1)
"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
$423 nightly
The price is $483
Dec 11 - Dec 12
Total with taxes and fees
Luxury NY Home with Free Parking
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Vacation Home in North End

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
$1,403 nightly
The price is $1,587
Dec 11 - Dec 12
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Microwave, oven, stovetop, dishwasher
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

Vacation Home in Norwalk

3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
7.0 out of 10, Good, (2)
"This was a great house to stay in as we visited family whose house had a strict no dogs allowed in the house rule. The beds were comfortable and the house was clean and updated. We only stayed upstairs, we didn’t have a use for the in law apartment downstairs, but I loved that the backyard was fenced in and clean. We’ll be back again, maybe when the pool is open and the weather warmer and we would recommend the place for anyone looking for a clean, updated place to stay."
United States
Crystal S.
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Vacation Home in Redding

Peaceful Vintage Home with Private Pond in Redding, CT.
2.0 star property
9.4 out of 10, Exceptional, (3)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
$570 nightly
The price is $646
Dec 15 - Dec 16
Total with taxes and fees
Peaceful Vintage Home with Private Pond in Redding, CT.
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$172 nightly
The price is $195
Dec 11 - Dec 12
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Lounge
Luxury Apartments by Hyatus White Plains

Aparthotel in White Plains

Luxury Apartments by Hyatus White Plains
4.5 star property
10.0 out of 10, Exceptional, (1)
"xcellent experience! The room was spotless and beautifully designed, it honestly blew me away. The staff was courteous and attentive to every detail. It’s rare to find a place that ticks every box, but this one did. Thank you for a fantastic few days!"
United States
Michael
Luxury Apartments by Hyatus White Plains
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$256 nightly
The price is $277
Dec 11 - Dec 12
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC
Interior
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Aparthotel in Ossining

1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
$245 nightly
The price is $279
Dec 14 - Dec 15
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Fridge, microwave, oven, stovetop
Luxury 6 Bedrooms House

Villa in West Norwalk

Luxury 6 Bedrooms House
10.0 out of 10, Exceptional, (3)
"Lots of space and very convenient "
United States
Michael J.
$830 nightly
The price is $941
Jan 3 - Jan 4, 2026
Total with taxes and fees
Luxury 6 Bedrooms House
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 Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Hotel appearance notibly better c/w last visit. Clean, excellent rooms, great staff. Gym was utile and clean. definitely will return next time."
Christopher 2-night trip
Posted 1 day ago
Hyatt Regency Greenwich

Find out more about New Canaan

Everything you need to know about New Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Canaan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Canaan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Canaan. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Canaan rentals

At Expedia, we put the best New Canaan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Canaan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in New Canaan?

Yes, you can find vacation rentals in New Canaan near Goldenberry, or you can go with a secluded option if you want a relaxing stay. New Canaan is known for its seafood restaurants.

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: Visitors like this New Canaan vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in New Canaan?

With 6 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 Silvermine Arts Center, whereas Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Glass House Visitor's 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.