A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
$867 nightly
The price is $981
Aug 26 - Aug 27
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (165 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$134 nightly
The price is $155
Aug 30 - Aug 31
Total with taxes and fees
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. 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
$219 nightly
The price is $252
Aug 25 - Aug 26
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.

4. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (110 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$233 nightly
The price is $268
Sep 13 - Sep 14
Total with taxes and fees
DUNE Fairfield Beach
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

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

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
$319 nightly
The price is $361
Aug 25 - Aug 26
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

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

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
$677 nightly
The price is $766
Sep 14 - Sep 15
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A swimming pool with a stone wall and greenery, a covered patio with outdoor furniture, and a stone building with a tiled roof.

7. Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
New Canaan
10.0 out of 10, Exceptional, (42 reviews)
"Unique home with beautiful grounds and classically designed interior. Perfect for relaxing and enjoying with family/friends."
United States
David
$1,924 nightly
The price is $2,180
Sep 7 - Sep 8
Total with taxes and fees
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
A modern kitchen with white cabinets, a marble island, and black bar stools.

8. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
$630 nightly
The price is $713
Sep 16 - Sep 17
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
A bedroom with a bed, a round mirror, a door, and wall decorations.

9. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
$309 nightly
The price is $350
Aug 29 - Aug 30
Total with taxes and fees
2-bedroom apartmet No cleaning Fee
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

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.
$371 nightly
The price is $420
Aug 25 - Aug 26
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A campfire with a wooden table and benches by a lake.

11. 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, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
$334 nightly
The price is $377
Sep 24 - Sep 25
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A living room with a sofa set, a coffee table, and a television on a stand.

12. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (8 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$533 nightly
The price is $603
Aug 31 - Sep 1
Total with taxes and fees
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

13. 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)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
$986 nightly
The price is $1,047
Aug 25 - Aug 26
Total with taxes and fees
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

14. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
$864 nightly
The price is $917
Sep 1 - Sep 2
Total with taxes and fees
5BR Beach House, Water Views, Game Room, Backyard
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.

15. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"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.
$319 nightly
The price is $361
Aug 29 - Aug 30
Total with taxes and fees
Modern Luxury 1BR Stamford Getaway

16. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"Great stay!"
United States
Kyra S.
$1,206 nightly
The price is $1,279
Aug 29 - Aug 30
Total with taxes and fees
5BR Beach House, Game Room + Huge Backyard
A modern kitchen with a central island, pendant lights, and built-in shelves.

17. Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
$560 nightly
The price is $634
Aug 26 - Aug 27
Total with taxes and fees
Stylish Home and Cozy
A modern living room with a sofa, a coffee table, and a bar stool.

18. 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.
$279 nightly
The price is $316
Aug 29 - Aug 30
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

19. 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
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$336 nightly
The price is $381
Sep 8 - Sep 9
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A living room with a piano, a white sofa, a coffee table, and a lamp.

20. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
$629 nightly
The price is $712
Sep 14 - Sep 15
Total with taxes and fees
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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

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 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.

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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 New Canaan Town Hall 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.