New Canaan Holiday Rentals from AU$221: Search Short-Term Rentals

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Our top choices for New Canaan holiday rentals

A room with a wooden floor, a black leather chair, a piano, and a large window with a view of a deck and trees.

1. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

New Canaan

Kaia W.

includes taxes & fees

4 Nov - 5 Nov

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Historic District

Ronbert

includes taxes & fees

20 Oct - 21 Oct

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

Fairfield Beach

slava

includes taxes & fees

29 Oct - 30 Oct

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

4. Stamford Suites

Downtown Stamford

Alice

includes taxes & fees

18 Oct - 19 Oct

5. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Downtown Stamford

Marisa C.

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

6. Spacious Studio with Pool Table

Westport

Eadweard

A modern living room with a sofa, a coffee table, and a bar stool.

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

Downtown Stamford

michelle b.

includes taxes & fees

27 Oct - 28 Oct

A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

8. Modern Apartment with Private Entrance

Historic District

Derek H.

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

9. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

includes taxes & fees

16 Oct - 17 Oct

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

includes taxes & fees

15 Nov - 16 Nov

A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

11. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Historic District

Ricky W.

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a central island, pendant lights, and built-in shelves.

12. Stylish Home With Free ParkingZA

Glenbrook-Belltown

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinetry, a stainless steel refrigerator, a dishwasher, and a microwave.

13. Gilded Age Luxury Surrounded by Nature

Cranbury

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinets, a marble island, and black bar stools.

14. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Linda S.

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a bed, a nightstand, a dresser, a window with blinds, and a radiator.

15. Gem by the water+ firepit and all fenced backyard

Waterside

Leslie S.

includes taxes & fees

20 Oct - 21 Oct

16. Stylish Home and Cozy200

Downtown Stamford

includes taxes & fees

3 Nov - 4 Nov

A living room with a sofa set, a coffee table, and a television on a stand.

17. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

includes taxes & fees

16 Oct - 17 Oct

A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

18. Nama-stay, sweet pink Saugatuck Shores beach cottage

Westport

Deb S.

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

19. Modern Luxury 1BR Stamford Getaway

Downtown Stamford

"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...

Debbie N.

includes taxes & fees

28 Oct - 29 Oct

A modern living room with a fireplace, a television, and a dining area with chairs and a table.

20. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

Melissa H.

includes taxes & fees

19 Oct - 20 Oct

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Top New Canaan Hotel Reviews

Tarrytown House Estate

8/10 Good

"Bathroom had an odor, the toilet kept running. It got fixed but took two requests. I would have appreciated that was addressed prior to our arrival. The lid was on backwards so there was an indication of awareness. However the room was very clean and the staff were all polite and receptive when interacting with our feedback. Good location for all the wonderful tourism and restaurants as well."

Hyatt Regency Greenwich

8/10 Good

"The property is very pretty. Unfortunately the greenhouse style ceiling in the lobby was leaking due to heavy rain. The rooms were clean but the bathroom needs some work. Not quite clean enough for my standards. It needs some freshening up. The staff is friendly. Breakfast was ok but the staff seems to need more training to meet the standards of this type of hotel."

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, 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 favourite 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 depend 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 AU$221 per night. Entering your travel dates in the search wizard might find you 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?

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!: This holiday home rental outside of New Canaan is located on a lake, and has a fireplace, a patio 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 a selection of games.

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 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.

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Check prices for these dates

Our top choices for New Canaan holiday rentals

1. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

2. Guesthouse at Norwalk Inn

3. DUNE Fairfield Beach

4. Stamford Suites

5. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

6. Spacious Studio with Pool Table

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

8. Modern Apartment with Private Entrance

9. Modern Luxe 1BR Apt in Downtown Stamford

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

11. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

12. Stylish Home With Free ParkingZA

13. Gilded Age Luxury Surrounded by Nature

14. Spacious Retreat with Game Room and Fire Pit

15. Gem by the water+ firepit and all fenced backyard

16. Stylish Home and Cozy200

17. Spacious Stamford Home | Family, Work, Parking

18. Nama-stay, sweet pink Saugatuck Shores beach cottage

19. Modern Luxury 1BR Stamford Getaway

20. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Find holiday rentals that suit your style

Top New Canaan Hotel Reviews

Tarrytown House Estate

The Armon Stamford Hotel & Conference

Hyatt Regency Greenwich

Baymont by Wyndham White Plains - Elmsford

The Circle Hotel Fairfield

Find out more about New Canaan

Frequently asked questions

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