New Canaan Vacation Rentals from CA $215: Short-Term Rentals for 2026

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

Charming Home in Seaside : Visitors like this New Canaan vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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In two weeks

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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

Downtown Stamford

Alice

CA $251 total

includes taxes & fees

Sep 30 - Oct 1

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

2. Guesthouse at Norwalk Inn

Historic District

Ronbert

CA $461 total

includes taxes & fees

Oct 6 - Oct 7

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

CA $375 total

includes taxes & fees

Oct 5 - Oct 6

A modern living room with a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

4. Spacious Studio with Pool Table

Westport

Eadweard

CA $359 total

includes taxes & fees

Sep 28 - Sep 29

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.

CA $446 total

includes taxes & fees

Oct 4 - Oct 5

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

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

Waterside

Leslie S.

CA $467 total

includes taxes & fees

Sep 30 - Oct 1

A campfire with a wooden table and benches by a lake.

7. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

CA $443 total

includes taxes & fees

Oct 5 - Oct 6

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

8. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

CA $588 total

includes taxes & fees

Oct 2 - Oct 3

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

9. Gilded Age Luxury Surrounded by Nature

Cranbury

CA $608 total

includes taxes & fees

Sep 28 - Sep 29

A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

10. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Downtown Bridgeport

Bailey

CA $328 total

includes taxes & fees

Sep 28 - Sep 29

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

11. Stylish Home and Cozy200

Downtown Stamford

CA $406 total

includes taxes & fees

Sep 28 - Sep 29

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

12. Romantic Hide Out

Waterside

Cheryl H.

CA $341 total

includes taxes & fees

Sep 29 - Sep 30

A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

13. Luxury Designer 2 bedroom+office/3bed vacation home.

Brooklawn - St. Vincent

Anonymous traveller

CA $560 total

includes taxes & fees

Sep 28 - Sep 29

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

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

Historic District

Melissa H.

CA $944 total

includes taxes & fees

Sep 29 - Sep 30

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

15. Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan

bill J.

CA $775 total

includes taxes & fees

Sep 29 - Sep 30

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

16. 5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

Maury A.

CA $1,032 total

includes taxes & fees

Sep 30 - Oct 1

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

17. Modern 2 Bed in BlackRock

Black Rock Historic District

Joshua L.

CA $475 total

includes taxes & fees

Sep 28 - Sep 29

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

18. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

CA $814 total

includes taxes & fees

Oct 4 - Oct 5

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.

CA $510 total

includes taxes & fees

Oct 4 - Oct 5

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

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

Historic District

Ricky W.

CA $543 total

includes taxes & fees

Oct 25 - Oct 26

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Top New Canaan Hotel Reviews

Sheraton Tarrytown Hotel

10/10 Excellent

"Enjoyed the property and have stayed there before and will again"

Amsterdam Hotel

10/10 Excellent

"I am a repeat guest at Amsterdam Hotel starting over five years ago. This is a family-owned and family-run hotel. They are always superb. I live in Hawaii, where we take our "Aloha" seriously. The staff certainly have that "Aloha Spirit we cherish and practice. Thank you, as always -now and in the future. The breakfast provided is appreciated. :)"

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

10/10 Excellent

"This was my first time at this hotel. I had heard good things about it from others. There was what I'd call a glitch in my checking-in. The gentleman at the front desk handled this professionally and all went well. The room was very clean and just what I needed for my stay. The breakfast provided was much more than I expected. The location is ideal, though I should mention that parts of the street do not have adequate sidewalks or crossing signals for pedestrians. There is a large Shop-Rite grocery and other shops nearby. I will be back."

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Canaan vacation rentals we have selected for you start as low as CA $215 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 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.

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?

Charming Home in Seaside: Visitors like this New Canaan vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Old Stamford Road Bird Sanctuary and God's Acre 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.

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Check prices for these dates

Our top choices for New Canaan vacation rentals

1. Stamford Suites

2. Guesthouse at Norwalk Inn

3. DUNE Fairfield Beach

4. Spacious Studio with Pool Table

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

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

7. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

8. Modern Luxe 1BR Apt in Downtown Stamford

9. Gilded Age Luxury Surrounded by Nature

10. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

11. Stylish Home and Cozy200

12. Romantic Hide Out

13. Luxury Designer 2 bedroom+office/3bed vacation home.

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

15. Seabreeze at the beach west beach Stamford ct.

16. 5BR Beach Home | Walk to Cove Beach + Private Yard

17. Modern 2 Bed in BlackRock

18. Spacious Stamford Home | Family, Work, Parking

19. Modern Luxury 1BR Stamford Getaway

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

Find vacation rentals that suit your style

Top New Canaan Hotel Reviews

Sheraton Tarrytown Hotel

Sleepy Hollow Hotel, a Dolce by Wyndham

Amsterdam Hotel

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

The Circle Hotel Fairfield

The Stamford Hotel

Find out more about New Canaan

Frequently asked questions

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