House vacation 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 Massapequa
4.93 out of 5 average rating, 123 reviews

Great Family Times in this 5 Bedroom House

JorgeRating, 5 stars1 month ago
My family and I had a beautiful stay and I couldn’t have asked for a better rental. The Airbnb was huge with more than enough room for everyone and the backyard was large and spacious enough to have everyone eat comfortably. If I ever need another large rental you can bet I’m gonna check here first.
Top guest favourite
Home in Warwick
4.98 out of 5 average rating, 61 reviews

4 bedroom house with pool (Kids & Dog Friendly)

MichelleRating, 5 stars1 week ago
Betty was so quick to help when our original location to stay was cancelled. I am so thankful her property was available and how easy she made the process after what we went through!
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars3 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Guest favourite
Home in Newburgh
4.83 out of 5 average rating, 81 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars2 weeks ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 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 Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Guest favourite
Home in Westhampton
5 out of 5 average rating, 13 reviews

1940’s Westhampton renovated bungalow

FarbodRating, 5 stars8 months ago
Sarah was wonderful as a host and the home was very well maintained in a beautiful neighborhood. Thank you!
Guest favourite
Home in Englewood
4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars2 weeks ago
This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

Weekly house rentals

Guest favourite
Home in White Plains
4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

ShannonRating, 5 stars7 months ago
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.
Superhost
Home in Greenwood Lake
4.84 out of 5 average rating, 109 reviews

Sunset on the lake front/Kayak Permit#34323

DianaRating, 5 stars2 weeks ago
Wonderful and responsive host and very accommodating. Beautiful quiet house oversee the lake. Exactly as like the picture.
Superhost
Home in Wallkill
4.86 out of 5 average rating, 121 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

RobertoRating, 5 stars1 month ago
I had a wonderful stay at this beautiful modern home in Wallkill, NY. Tucked away on a quiet street with plenty of privacy from the surrounding trees, it felt like the perfect escape from the city. My favorite part was the open-concept kitchen and living area, with expansive windows that made it feel like I was immersed in nature while still enjoying the comfort of being indoors. It was the ideal space to rest, relax, and recharge. If you're looking for a peaceful getaway, I highly recommend this home!
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars1 month ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Top guest favourite
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars2 weeks ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Guest favourite
Home in Syosset
4.9 out of 5 average rating, 51 reviews

Elegant, resort style, clean, north shore home

FredRating, 5 stars9 months ago
The inside and outside areas were meticulously maintained. The weather was great, so we were able to really enjoy the pool and deck. Michelle was extremely responsive and did a great job with instructions, recommendations, and communications. One member of our party needed to work a few days, and the office space in the basement was perfect.
Top guest favourite
Home in Cos Cob
5 out of 5 average rating, 16 reviews

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

AnishRating, 5 stars2 months ago
This is our 2nd review Victoria’s properties and we just want to reiterate how special of a landlord Victoria is. The best. I cannot recommend her properties enough if you are in need of a Greenwich rental like we were.
Guest favourite
Home in Highland Falls
4.97 out of 5 average rating, 61 reviews

West Point Hudson Valley Getaway

TimRating, 5 stars5 months ago
We stayed at Patrick’s place to attend an Army football game. Everything was perfect and easy. It’s really close to campus/post. It’s a nice little town and close to Cold Spring where we had lunch on Friday. Thanks for a great weekend.

Private house rentals

Superhost
Home in Bayonne
4.89 out of 5 average rating, 9 reviews

Entire Home Near Manhattan Parking

MufizaRating, 5 stars3 weeks ago
We had a great family stay at this bnb.. our big family travelled from several different countries for a wedding and this was a great place to stay. Feels like home, had all the amnesties that such a big family would need. Very very spacious. And the host was very responsive. The neighbourhood was peaceful and quite, yet two streets away on a walkable distance you find great Resturant with all kind of cuisines including Italian (quite a few), sushi, shawarma, ice cream shops and Francine. Train station is a walkable distance. Costco and lidl was also in a short drivable distance.
Top guest favourite
Home in Philipstown
4.93 out of 5 average rating, 129 reviews

Cozy 3 bedroom house on quiet private road

ScottRating, 5 stars1 month ago
Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars1 month ago
It was wonderful stay and I’d go back anytime
Superhost
Home in Amityville
4.72 out of 5 average rating, 74 reviews

Cheerful 2-Bedroom Home With On Premises Parking

SharozRating, 5 stars5 months ago
Very respectable, responsive and courteous couple! Proactive in solving your issues. Felt like home
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top guest favourite
Home in Philipstown
5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars5 months ago
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)
Guest favourite
Home in Stratford
4.94 out of 5 average rating, 174 reviews

Cozy Colonial - Private Hot Tub & Entire House

MonicaRating, 5 stars1 month ago
We loved our stay! Dylan was extremely responsive and the home was exactly as explained. The rooms were spacious and the beds were so comfy! No complaints! We will definitely stay again when we visit family.
Top guest favourite
Home in Brookhaven
4.96 out of 5 average rating, 185 reviews

Beautiful & Independent Guest House near the water

HeatherRating, 5 stars1 week ago
We had a wonderful weekend at Raphael's cottage. It's beautiful & the setting is landscaped like a little paradise. He was responsive to any question we had. The yard for the cottage is adjacent to the main yard, but is separated by hedges. It was so relaxing to sit at the outdoor table on the sunny days we had-our pup enjoyed it, too! We explored the immediate area when walking our dog, and in about 15 minutes had reached the ocean, a pleasant surprise! There is also a wooded trail very nearby the house which I enjoyed. The king size bed was comfortable, and on the chilly April nights we had the heating was immediately responsive. The shower itself wasn't pictured in the listing photos, and in reality was very small. We hadn't inquired on it in advance-so it was a surprise-but certainly adequate. Overall, we had a great experience & felt right at home & comfortable. We would definitely recommend Raphael's place to those who find themselves in the area!

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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