New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for New Canaan vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfastā€¦bagels and coffeeā€¦help your self. One plus small kitchenette"
United States
Christine
The price is AEDĀ 599
AEDĀ 689 total
includes taxes & fees
19 Nov - 20 Nov
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AEDĀ 1,121
AEDĀ 1,289 total
includes taxes & fees
9 Nov - 10 Nov
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AEDĀ 647
AEDĀ 968 total
includes taxes & fees
9 Dec - 10 Dec
DUNE Fairfield Beach
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

4. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is AEDĀ 1,208
AEDĀ 1,855 total
includes taxes & fees
9 Nov - 10 Nov
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A modern kitchen with a large island, wooden cabinets, and pendant lighting.

5. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is AEDĀ 3,385
AEDĀ 4,839 total
includes taxes & fees
24 Nov - 25 Nov
Stareway to Heaven in Fairfield
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

6. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AEDĀ 2,297
AEDĀ 3,928 total
includes taxes & fees
9 Nov - 10 Nov
Beechmont - Perfect for Family Retreat!
A breakfast buffet with pastries, fruits, and a coffee station.

7. 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 didnā€™t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is AEDĀ 3,306
AEDĀ 4,229 total
includes taxes & fees
9 Nov - 10 Nov
3BR Prime Luxury NY - Free Parking
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

8. 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 AEDĀ 2,237
AEDĀ 3,399 total
includes taxes & fees
9 Nov - 10 Nov
4 Mi to Beach & Dtwn! Charming Fairfield Home
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AEDĀ 1,802
AEDĀ 3,748 total
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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

A wooden interior with a reception desk, framed botanical prints, and a sign reading "The Water."
The Watershed

The Watershed

The Watershed
Cranbury

10/10 Excellent

Beautiful hotel! We would definitely stay again.
United States
Donna
Reviewed June 24, 2025
The Watershed

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.

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

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!: Visitors like this New Canaan vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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 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.