House holiday rentals in New Canaan

Find and book unique houses on Airbnb

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Popular amenities for New Canaan house rentals

House rentals with a pool

Guest favourite
Home in Patchogue
4.93 out of 5 average rating, 126 reviews

Joyful Beach House, viewing The Great South Bay

DanielRating, 5 stars2 weeks ago
Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!
Top Guest favourite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars3 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
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!
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars3 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 Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars1 week ago
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars1 day ago
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Weekly house rentals

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

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Top Guest favourite
Home in Norwalk
5 out of 5 average rating, 54 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

DennyseRating, 5 stars1 week 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 East Norwalk
4.95 out of 5 average rating, 21 reviews

Family friendly

DarrenRating, 5 stars1 week 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!
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.
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
Guest favourite
Home in Redding
5 out of 5 average rating, 36 reviews

Quiet and Cozy Cottage near NYC with a Pond

LouiseRating, 5 stars3 weeks ago
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.
Top Guest favourite
Home in Bedford
5 out of 5 average rating, 39 reviews

Comfortable Mid-Century on Quiet Country Road

BessRating, 5 stars1 week ago
Adam provided a beautiful home with everything you could ask for to have a lovely stay. The beds were very comfortable, it was spacious and clean. He was responsive and gave clear instructions for check in/out and using the various amenities. I would definitely recommend him as a host!
Guest favourite
Home in Norwalk
4.89 out of 5 average rating, 38 reviews

Entire House on Scenic Estate with Private Pond

JaeRating, 5 stars2 weeks ago
This space was absolutely amazing. It was clean quiet and incredibly beautiful. As we sat looking out over the pond a young male deer with little stubby horns walked by, stopped to stare at us for a while, and then moved on. Obviously we already booked our return trip to stay again. I highly recommend this space to personal and business travelers. Enjoy!!!!

Private house rentals

Guest favourite
Home in Easton
5 out of 5 average rating, 29 reviews

Historic Designer City Getaway

FayRating, 5 stars3 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 Pound Ridge
4.86 out of 5 average rating, 49 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

PaulRating, 5 stars2 months ago
We had a great time at this lovely, antique home, complete with gardens and great big back yard! Bob, our Corgi, definitely approved! Easy access to Stamford and Bedford! Thanks for your thoughtful arrangements!
Guest favourite
Home in Stamford
4.92 out of 5 average rating, 66 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 stars3 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 Stamford
4.96 out of 5 average rating, 24 reviews

Modern Tranquil Home In Connecticut- 40 min to NYC

RogerRating, 5 stars1 month ago
The location and house is etremely peaceful and safe, in the middle of nature. Our stay was wonderful and extremely comfortable. We had an excellent time. This is a return stay and we would stay again. It feels like home. Phylilis is very helpful and resppnsive. Overall a great experience. 5 star.
Superhost
Home in Rowayton
4.78 out of 5 average rating, 9 reviews

Coastal Comfort in Rowayton, CT

FawziaRating, 5 stars1 month 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 stars4 days 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

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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