House holiday rentals in New Canaan

Find and book unique houses on Airbnb

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Popular amenities for house rentals in New Canaan

House rentals with a pool

Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars4 weeks ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Guest favourite
Home in Patchogue
4.93 out of 5 average rating, 125 reviews

Joyful Beach House, viewing The Great South Bay

JoannaRating, 5 stars3 weeks ago
The beach house was perfect, just as described. It was clean and very homely, in a lovely location. Natasha was a great host from start to finish. Would definitely recommend to friends/family looking for a place to stay in Patchogue. Many thanks Natasha
Superhost
Home in Hampton Bays
4.94 out of 5 average rating, 131 reviews

Peaceful Retreat in Immaculate Architect’s House

JessikahRating, 5 stars1 month ago
Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 139 reviews

GOOD VIBEZ HOUSE! Golf-Heated Pool-HotTub-GameRm!

AliceRating, 5 stars2 weeks ago
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars2 weeks ago
Only complaint would be the noise from road during the morning commute
Superhost
Home in Beacon
4.92 out of 5 average rating, 133 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

MarissaRating, 5 stars2 weeks ago
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.

Weekly house rentals

Superhost
Home in Pound Ridge
4.63 out of 5 average rating, 8 reviews

Beautiful Secluded Contemporary

PaulRating, 5 stars5 months ago
This house is perfect for families to gather, spend time by the fireplace, share meals with the center island kitchen and dining tables, and enjoy each other’s company. Corinne is the perfect host, responsive, communicative, welcoming, warm. Pound Ridge is a wonderful town and the reservoir, quiet roads, trees, wildlife, walking trails, and stone walls are the perfect place to relax and get away from the city.
Guest favourite
Home in Norwalk
4.96 out of 5 average rating, 50 reviews

Modern Nature Retreat

MarkRating, 5 stars5 months ago
Beautiful house, great place for a relaxing weekend
Top guest favourite
Home in Norwalk
5 out of 5 average rating, 54 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

DennyseRating, 5 stars6 days ago
It’s obvious that Scott and Wendy have put a lot of thought and effort into making their place more than just functional. It is also comfortable and attractive. My husband and I just hope it’s available the next time we visit our grandkids!
Top guest favourite
Home in Norwalk
4.95 out of 5 average rating, 20 reviews

Family friendly

DarrenRating, 5 stars6 days ago
Really enjoyed this stay. The property was very clean and the decor was superb. Would highly recommend this Airbnb for future reference. Communication was fast and sufficient!
Guest favourite
Home in Easton
5 out of 5 average rating, 29 reviews

Historic Designer City Getaway

FayRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay at this historic house. It is full of character: we especially loved the massive fireplace where meals were presumably prepared back when it was an inn in the 1700s. It is also ridiculously spacious and very well furnished and equipped for a group of 10: the dining table easily seats 10, there is ample comfortable seating in the living room (not to mention at least 3 other sitting rooms one could gather in), and 8 of us were simultaneously cooking in the kitchen without anyone bumping elbows. Cooking here is a dream: there is a 6-burner+grill stove, 2 ovens, and all the equipment you could want (including a KitchenAid stand mixer and Vitamix blender). Moreover, Carly was an excellent host: she was always quick to respond, her messages were clear, and she generously allowed us to stay an extra hour to make our timing work out well. We highly recommend this house and would love to return.
Superhost
Home in Norwalk
5 out of 5 average rating, 4 reviews

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br

TomRating, 5 starstoday
Andrea's house was perfect for our family! The house is recently updated and very spacious. It's a great place if you want to be a 5min drive to everything in Norwalk!
Guest favourite
Home in Bedford
4.93 out of 5 average rating, 84 reviews

Bedford Paradise Getaway | Hot Tub | Town Center

LaurenRating, 5 stars1 week ago
Cozy home, well located to pop into Bedford Village for morning coffee and a casual dinner. Perfect launchpad to spend a weekend exploring. Styled by an interior designer.
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 37 reviews

Historic wooded 3BD 1 hour from NYC

SabrinaRating, 5 stars1 month ago
We had the most magical stay at Keely’s place. Her home is beautiful and smelled amazing. Thriving plants, surfaces of wood and stone - a true naturalist’s refuge. The picture windows overlooked gardens bursting with flowers. We meandered from the backyard onto hiking trails through the woods, lounged on the deck in the sun and savored the tranquility. Perhaps the best Airbnb we’ve ever encountered. 10/10

Private house rentals

Guest favourite
Home in Stamford
4.94 out of 5 average rating, 65 reviews

Spacious Home - Center Of Stamford

MaryRating, 5 stars1 month ago
This home was fantastic! Absolutely immaculate and it offered everything we needed. We live close by and this was a perfect place for family to stay while visiting for Easter! As a matter of fact, the host put Easter eggs all around and the children were thrilled. Such attention to detail. Would highly recommend!
Guest favourite
Home in Stamford
4.98 out of 5 average rating, 61 reviews

Gameroom, backyard + pool! 7m to train + downtown

RebeccaRating, 5 stars2 weeks ago
Everything was clean, just a few glitches with dining room lights and needed more towels. Otherwise everything was great!
Guest favourite
Home in Shippan Point
4.96 out of 5 average rating, 49 reviews

Seashell Bungalow | 3 Bed 1 Bath | Beach House

DorisRating, 5 stars1 week ago
Beautiful place. Pristine. Comfortable Short walk to the beach. Unfortunately because of rain we didn’t get to enjoy the lovely back yard. Owners were very good at getting back to us with any questions we had And being able to have a later check out really helped! Would definitely recommend this home and would love to find a reason to ho back again!!
Superhost
Home in Westport
4.67 out of 5 average rating, 3 reviews

Boho Chic Private Home in the Heart of Westport CT

ClaudiaRating, 5 stars3 weeks ago
Emma and Nick were so welcoming. The entire property has an amazing vibe and peaceful surroundings. The kitchen had all the basics needed. The rooms were very comfortable. You felt like you were in the country but we were a short drive to everything. The entire area was just very charming. Emma and Nick deserve a super host rating for sure.
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 38 reviews

Private farm cottage +hiking

SandyRating, 5 stars3 months ago
We spent six great weeks at Fabien and Christy's cottage while relocating to the area. We loved everything about our time there including the very comfortable bed and furniture and the well stocked kitchen. We were there during a very cold stretch and the house stayed warm and cozy. The wood burning stove was a fun treat on cold snowy days. Fabien and Christy were wonderful hosts making sure we had everything we needed and helped with information about the area. We spent a lot of time exploring the beautiful property with our dog. It's a very peaceful spot and still only a short drive to many towns with lots of great restaurants and shopping. I would definitely recommend Fabien and Christy's cottage to anyone looking for a short or long stay in the area.
Superhost
Home in Rowayton
4.78 out of 5 average rating, 9 reviews

Coastal Comfort in Rowayton, CT

FawziaRating, 5 stars3 weeks ago
The house was just as described and just as the photos show. Spotlessly clean. Comfortable beds, linens and pillows. Pretty neighborhood, and peaceful.
Guest favourite
Home in South Norwalk
4.97 out of 5 average rating, 67 reviews

Chic Historic Home w/Water View

JeffRating, 5 stars1 month ago
Comfortable, quiet, clean, and well appointed, this home was the perfect day for my family for a wedding week. Highly recommend it. Kim communicated really well and was very attentive. A+
Guest favourite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars1 day ago
A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

Quick stats about house rentals in New Canaan

  • Total rentals

    20 properties

  • Total number of reviews

    310 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

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