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 Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
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 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 Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
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 stars4 days 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.
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

Top Guest favourite
Home in Norwalk
4.95 out of 5 average rating, 22 reviews

Family friendly

ColbyRating, 5 stars2 days ago
Excellent space for our group - easy to get in & out, had everything we needed, & plenty of room.
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 Norwalk
4.8 out of 5 average rating, 5 reviews

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br

TomRating, 5 stars6 days ago
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, 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
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 stars3 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

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.
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars2 months ago
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!
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 Wilton
4.95 out of 5 average rating, 21 reviews

Nature Retreat on 2.5 Acres

Leigh AnnRating, 5 stars1 week ago
Stayed at Klaira’s place for a long weekend while visiting family in the area. The house was clean, spacious, and had all the necessary amenities. We thoroughly enjoyed our stay.
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, 68 reviews

Chic Historic Home w/Water View

JaimeRating, 5 stars1 month ago
Really enjoyed my stay! Would recommend for anyone looking for a place to stay in the area. Thanks Kim - for hosting us.
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 week 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

Destinations to explore