A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for New Canaan vacation 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!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.6 out of 10, Exceptional, (9 reviews)
"lovely porch and backyard."
United States
Kaia W.
$916 nightly
The price is $1,043
Nov 4 - Nov 5
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$294 nightly
The price is $339
Oct 14 - Oct 15
Total with taxes and fees
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, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Oct 19 - Oct 20
Total with taxes and fees
DUNE Fairfield Beach
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

4. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (191 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$139 nightly
The price is $160
Oct 13 - Oct 14
Total with taxes and fees
Stamford Suites
Private kitchen

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

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
$239 nightly
The price is $271
Oct 13 - Oct 14
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern living room with a sofa, a coffee table, and a bar stool.

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

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
$275 nightly
The price is $312
Oct 18 - Oct 19
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A room with large windows overlooking a lake and greenery.

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
$308 nightly
The price is $349
Oct 14 - Oct 15
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
$293 nightly
The price is $331
Oct 13 - Oct 14
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$368 nightly
The price is $417
Oct 15 - Oct 16
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

10. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$380 nightly
The price is $430
Oct 13 - Oct 14
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

11. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
10.0 out of 10, Exceptional, (1 review)
"This was a great deal on the busy weekend we stayed. The space was even better than described."
United States
Derek H.
$261 nightly
The price is $297
Oct 13 - Oct 14
Total with taxes and fees
Modern Apartment with Private Entrance
A modern kitchen with a central island, pendant lights, and built-in shelves.

12. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
$271 nightly
The price is $307
Nov 3 - Nov 4
Total with taxes and fees
Stylish Home With Free ParkingZA
A dining table set with blue bowls, gold cutlery, and yellow lemons.

13. Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
$214 nightly
The price is $242
Oct 15 - Oct 16
Total with taxes and fees
Romantic Hide Out
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (18 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
$538 nightly
The price is $609
Oct 18 - Oct 19
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
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.

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (18 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
$205 nightly
The price is $232
Oct 13 - Oct 14
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern kitchen with white cabinets, a marble island, and black bar stools.

16. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
$709 nightly
The price is $803
Oct 28 - Oct 29
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
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

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
$659 nightly
The price is $700
Oct 14 - Oct 15
Total with taxes and fees
5BR Beach Home | Walk to Cove Beach + Private Yard
A swimming pool at night with blue lighting.

18. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$135 nightly
The price is $152
Oct 18 - Oct 19
Total with taxes and fees
Business or Weekend escape
A spacious living area with a modern sofa, a blue chair, and a wooden floor.

19. Elegant Home

Elegant Home
Downtown Stamford
$265 nightly
The price is $300
Oct 13 - Oct 14
Total with taxes and fees
Elegant Home
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.

20. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
8.0 out of 10, Very good, (2 reviews)
"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...
United States
Debbie N.
$317 nightly
The price is $359
Oct 13 - Oct 14
Total with taxes and fees
Modern Luxury 1BR Stamford Getaway
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"We didn't use much of the amenities so I cannot speak to that but the bed was the comfiest bed we've ever experienced. The front desk were friendly and the room was clean. The remote check-in/check-out was super convenient, too. We will absolutely stay again when visiting family."
Caeleigh 1-night trip
Posted less than an hour ago
The Circle Hotel Fairfield

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit New Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.