Holiday Rentals New Canaan from £118: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for New Canaan holiday rentals

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

1. Guesthouse at Norwalk Inn

Historic District

Ronbert

includes taxes & fees

25 Oct - 26 Oct

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

2. Stamford Suites

Downtown Stamford

Alice

includes taxes & fees

13 Oct - 14 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

12 Oct - 13 Oct

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

4. Spacious Studio with Pool Table

Westport

Eadweard

includes taxes & fees

20 Oct - 21 Oct

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

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

Downtown Stamford

michelle b.

includes taxes & fees

20 Oct - 21 Oct

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

includes taxes & fees

11 Oct - 12 Oct

A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

7. Gilded Age Luxury Surrounded by Nature

Cranbury

includes taxes & fees

12 Oct - 13 Oct

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

8. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Leslie S.

includes taxes & fees

13 Oct - 14 Oct

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

9. Modern Apartment with Private Entrance

Historic District

includes taxes & fees

13 Oct - 14 Oct

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

10. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

includes taxes & fees

15 Oct - 16 Oct

A dining table set with blue bowls, gold cutlery, and yellow lemons.

11. Romantic Hide Out

Waterside

Cheryl H.

includes taxes & fees

15 Oct - 16 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

3 Nov - 4 Nov

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

13. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Linda S.

includes taxes & fees

11 Oct - 12 Oct

A modern living room with a large window, a sofa, a coffee table, and a TV.

14. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Downtown Bridgeport

Destiny

includes taxes & fees

26 Oct - 27 Oct

15. Stylish Home and Cozy200

Downtown Stamford

includes taxes & fees

28 Oct - 29 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.

16. 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

12 Oct - 13 Oct

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

17. 5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

Maury A.

includes taxes & fees

14 Oct - 15 Oct

A rooftop pool area with lounge chairs, a swimming pool, and a view of a marina with boats.

18. Apt On Harbor with Balcony and Pool

South End

An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

19. Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan

bill J.

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

20. Modern 2 Bed in BlackRock

Black Rock Historic District

Joshua L.

includes taxes & fees

12 Oct - 13 Oct

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Top New Canaan Hotel Reviews

Amsterdam Hotel

8/10 Good

"The Amsterdam Hotel was a decent find near downtown Stamford. It offers an affordable, very clean & quiet stay with plenty of free onsite self parking. The room was relatively spacious & very clean. The decor & furnishings were older but comfortable. It did not have the convenient connectivity options most modern travelers need. Luckily I had an extension cord with power strip which accommodated charging our various devices on the night stands by the bed. The desk staff were nice & very helpful when engaged with questions about the area. The hotel provides a basic continental breakfast with individually wrapped muffins, bagels, toaster waffles, cold cereal bowls, regular coffee, hot water & orange juice. If you prefer decaf coffee &/or a hot breakfast, there are a few good neighborhood cafes & diners within a comfortable walking distance or relatively short drive from the hotel. All-in-all a pleasant experience & we would consider staying there again on a future visit to the area."

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent

"Location location location! Perfectly situated along Broadway between Irvington and Tarrytown/Sleepy Hollow. Also a lovely hotel, nice room, friendly staff, decent price. I thought the bed was excellent, breakfast was too expensive for what was available, but similar to other places so oh well. Not a deal breaker! Would definitely recommend and also would stay here again!"

Tarrytown House Estate

8/10 Good

"This stay was the perfect, spooky place for our stay! We had tickets to the Pumpkin Blaze event and saw that this was a local stay and we were so excited to be staying right up the street from Washington Irving’s home! Sleepy Hollow is also not that far and we had a peace of mind knowing that other parents with kids were staying on our floor. If you’re wanting a Stephen King’s The Shining vibe, this is the place for you. We absolutely LOVED it; my husband isn’t really a spooky seeking person, but he loved the vibe since we were entering the month of October and we wanted something Fall like. The estate has so many amenities and we greatly appreciated the $10 complimentary bucks for their front desk shop (we had ran out of milk). Pool was fun, outside games and seats was worth it and the restaurant was chef’s kiss. We’re even planning a couples weekend back to this place because we absolutely enjoyed our stay. Please keep in mind that this place is dated and has some dated carpet and beds, but the front desk workers will work with you on anything you need. Cairo was the nice, young man who checked us in and was super informative and helpful; he was even working the next morning to check us out; what a dedicated worker!"

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 £118 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?

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. Guesthouse at Norwalk Inn

2. Stamford Suites

3. DUNE Fairfield Beach

4. Spacious Studio with Pool Table

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

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

7. Gilded Age Luxury Surrounded by Nature

8. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

9. Modern Apartment with Private Entrance

10. Modern Luxe 1BR Apt in Downtown Stamford

11. Romantic Hide Out

12. Stylish Home With Free ParkingZA

13. Spacious Retreat with Game Room and Fire Pit

14. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

15. Stylish Home and Cozy200

16. Modern Luxury 1BR Stamford Getaway

17. 5BR Beach Home | Walk to Cove Beach + Private Yard

18. Apt On Harbor with Balcony and Pool

19. Seabreeze at the beach west beach Stamford ct.

20. Modern 2 Bed in BlackRock

Find holiday rentals that suit your style

Top New Canaan Hotel Reviews

Amsterdam Hotel

Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown House Estate

Norwalk Inn & Conference Center

Find out more about New Canaan

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in New Canaan

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for New Canaan holiday rentals

1. Guesthouse at Norwalk Inn

2. Stamford Suites

3. DUNE Fairfield Beach

4. Spacious Studio with Pool Table

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

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

7. Gilded Age Luxury Surrounded by Nature

8. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

9. Modern Apartment with Private Entrance

10. Modern Luxe 1BR Apt in Downtown Stamford

11. Romantic Hide Out

12. Stylish Home With Free ParkingZA

13. Spacious Retreat with Game Room and Fire Pit

14. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

15. Stylish Home and Cozy200

16. Modern Luxury 1BR Stamford Getaway

17. 5BR Beach Home | Walk to Cove Beach + Private Yard

18. Apt On Harbor with Balcony and Pool

19. Seabreeze at the beach west beach Stamford ct.

20. Modern 2 Bed in BlackRock

Find holiday rentals that suit your style

Top New Canaan Hotel Reviews

Amsterdam Hotel

Find out more about New Canaan

Frequently asked questions

Go further with the Expedia app