Holiday Rentals New Canaan from £112: Find Short-Term Rentals & Holiday Accommodations

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

Captain's Cottage - Cold Spring Harbor Water Views : This holiday home rental outside of New Canaan is located on the waterfront, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

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Our top choices for New Canaan holiday rentals

Beechmont - Perfect for Family Retreat!

North End

includes taxes & fees

25 May - 26 May

Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

Fairfield Beach

Samantha

includes taxes & fees

10 Jun - 11 Jun

Prime Luxe 3-BR NYC - Free Parking

White Plains

includes taxes & fees

25 May - 26 May

4 Mi to Beach & Dtwn! Charming Fairfield Home

Tunxis Hill

includes taxes & fees

25 May - 26 May

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

28 May - 29 May

3BR Prime Luxury NY - Free Parking

White Plains

Osmond

includes taxes & fees

25 May - 26 May

Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

Historic District

Ronbert

includes taxes & fees

24 May - 25 May

Luxury NYC Home Game Room Free Parking

White Plains

"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...

Jorge

includes taxes & fees

24 May - 25 May

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Top New Canaan Hotel Reviews

HYATT house White Plains

10/10 Excellent

"Very helpful and friendly staff"

La Quinta Inn & Suites by Wyndham Stamford / New York City

6/10 Okay

"It was okay experience. The property is outdated. They’re going through repairs and I’m upset because I figured my kids would have gone to the pool but all they’re renovation supplies are stored in the pool area. And then some of the items in the room have missing outlets"

Trumbull Marriott Shelton

8/10 Good

"Staff was nice and helpful. James, one of the members on staff was a great help!! Due to unexpected circumstances, travel became stressful for me. James helped sort out my reservations and helped put me to ease.Thank you!! My only complaint is I felt some of the furniture chairs/couches had too many stains and should be cleaned or replaced."

Hampton Inn White Plains/Tarrytown

6/10 Okay

"This hotel is very old and not well maintained. It is being kept clean inside but the furnishings and bathroom was very old. Also the outside maintenance is terrible: cracked sidewalks and parking areas not well paved. Fencing falling down. Also if you must stay here, request a room on the backside of the building because the highway traffic noise in the front is so loud it was almost impossible to fall asleep. On a positive note, the staff is very nice."

Hyatt Regency Greenwich

10/10 Excellent

"This is the former Conde Naste headquarters so the property is very stylish and impressive. It’s a huge hotel with a recent remodel so there are conferences on the weekdays and weddings on the weekends. I was there on a Monday, so it was quiet, perfect for a good nights sleep. Rooms are spacious, clean and well lit. I liked the quality of the shampoo etc. Some rooms face the interior atrium which I would probably not be comfortable in since there could be noise from the bar area."

Find out more about New Canaan

Everything you need to know about New Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Canaan holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Canaan holiday rentals we have selected for you start as low as £112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Canaan rentals

At Expedia, we put the best New Canaan holiday 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 holiday.

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.

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.

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

Captain's Cottage - Cold Spring Harbor Water Views: This holiday home rental outside of New Canaan is located on the waterfront, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

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 Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and New Canaan Town Hall 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.

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