If you were asked which city has the most “well-to-do” families in the United States, you’d be forgiven if you answered Los Angeles. After all, LA is oft associated with the glamour that Hollywood brings. However, it is actually New Canaan that is one of the most affluent cities in the US. In fact, in 2008, it held the ranking of highest median family income in the country. The city was the focal point of a modern design movement, which began in the late 1940s with the renowned Harvard Five, a group of five architects from the Harvard Graduate School of Design. They were pioneers in their field and largely responsible for the design of today’s modern house.
New Canaan is also known for its many fairs and festivals, such as the New Canaan Nature Center Fall Fair and Saint Mark’s May Fair. Visitors can also dive into all sorts of fun things to do in New Canaan, and for a few minutes, you can drive southward to find more interesting activities in Stamford. With Airbnb, you’ll have a chance to stay in one of the city’s modern homes or a rustic cottage in the countryside. Read on for our list of Airbnb vacation rentals in and near New Canaan, Connecticut.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 06, 2024.
1. Rustic cottage getaway (from USD 133)
Less than an hours’ drive north of NYC is this rustic cottage getaway. It has a beautiful flower garden and is surrounded by lush, green woods. It’s located in a suburban neighbourhood, but the town of Mount Kisco is just 3 miles (4.8 km) away, with plenty of shopping and dining options available.
Guests have the entire cabin to themselves and they are free to roam the outdoor space. Getting here is convenient, even if guests don’t drive. The metro is just five minutes away, while the area is served by Uber and Lyft.
Mount Kisco, New York, United States
19.56 km (12.2 mi) from Stamford Museum & Nature CenterSuperhostAccommodates: 2
Top guest reviews
Amenities & Room:
the cabin has a gorgeous view and is extremely spacious yet cozybeautiful space very comfortable and cosyi appreciated the small touches such as leaving coffee ready for us at the kitchencomfortable creative and calming we will definitely returni came expecting a cabin but this is truly a luxurious cottage getaway cozy and inspiredCleanliness:
everything was very clean and full of thoughtful touchesit was sparkling clean and the house has everything you needyou can tell she created her space with tlc - clean with beautiful art and comfortable vibesHost:
nina was a wonderful host she was very responsive and warmnina was a sweet and thoughtful hostnina was an amazing host & enjoyed chatting with hernina was a great host and we recommend visiting her spacenina is an amazing hostRead more reviewsLocation:
close to some great restaurantsit’s located extremely close to the train station which makes taking an uber super cheapgood location to visit blue hill at stone barnsclose to great hikes sculpture gardens and town is nearbynina's house is a perfect place to getaway from a busy city
2. Charming private room in a sea captain’s house (from USD 85)
This rental near New Canaan, CT, is a historical colonial house, which once belonged to a sea captain. It has been updated with modern amenities and sits on 1 acre (0.4 hectares) of land. Your private room comes with a queen bed. The bathroom is huge, with both a stand-up shower and full-sized bathtub, so you can have a soak in a relaxing bath. Common areas, like the living room, backyard and kitchen, are open for guests to access.
Norwalk, Connecticut, United States
9.98 km (6.2 mi) from Stamford Museum & Nature CenterSuperhostAccommodates: 2
Top guest reviews
Amenities & Room:
i loved the furnishings in the roomi highly recommend it to all even those skeptical of sharing a bathroom and kitchenthe room was large and comfortablethe room (#2) was spacious and beautifulthe bed was quite comfortable as wellCleanliness:
the room was clean and the bed was comfortableclean quiet welcoming original and very comfortablethe room and bathroom were extremely cleancommunication was a breeze and the house was tidy and pleasanta beautiful quiet house clean comfortable rooms convenient locationHost:
wonderful host and beautiful placealso the owner is very flexible and friendlyfriendly host cute and cozy homebeautiful home and host was very nicefirst of all the host was very friendly and conversationalRead more reviewsLocation:
the location in norwalk was perfectthis place is amazing it's well located in norwalk walking distance from the beachnice place to stay in a convenient locationeasy to get to from the train station (we didn't have a car)beautiful low-key neighborhood close to rowayton and sono
3. Historical, mid-century modern, Zen home (from USD 236)
With nature just steps outside and minimalist interiors, this is a beautiful house, with carefully-curated design features, to give guests a sense of Zen calm. It’s a perfect place to stay near New Canaan, CT for a solo traveller looking to find his purpose in life or for a couple searching for a romantic getaway.
Featured in Travel & Leisure magazine, the house comes with an outdoor pool. It is also convenient to access other places in the area, such as the Grace Farm Museum and the Glass House. LaGuardia Airport is 55 minutes away, while White Plains Airport takes less than 15 minutes to reach.
Stamford, Connecticut, United States
1.87 km (1.2 mi) from Stamford Museum & Nature CenterSuperhostAccommodates: 2
Top guest reviews
Amenities & Room:
the area around it has comfortable beach chairs and lounge chairsher place is wonderfully comfortable serene and artful we felt so lucky to be therei would certainly stay with her again especially in the warmer months when her pool is opengreat facility - olga is excellenythe pool is outrageously beautiful and the space is just so perfectCleanliness:
there were many clean towels in the bathroomeverything was so clean and neatthe place is unique clean and very relaxingthe pool was super clean and we had all to ourselvesthe space itself is very clean and stocked with everything you might need during a stayHost:
olga was a fantastic hostolga is an amazing hostolga is a great hostolga is a great hostolga is an awesome hostRead more reviewsLocation:
i highly recommend this locationa delightfully close out of nyc get awayit seemed to close for comfort to mestill close enough to stamford to create a convenient holidayi would highly recommend this location
4. Sunny room in a charming 1920s house (from USD 69)
The house may be built in the 1920s, but its interiors are minimalistic and charming. Guests will have a private room in this beautifully decorated home. The room is located on the second level and has a queen bed and ensuite shower. The bathroom is luxurious, with a large rain shower and double sinks.
There is a fireplace in the living room, which is great in the winter. In the summer, guests can make use of the grill on the deck for any BBQ evenings. The house is easily accessible from the I-95. The metro station is nearby and it is only two stops to NYC.
Norwalk, Connecticut, United States
10.37 km (6.5 mi) from Stamford Museum & Nature CenterAccommodates: 2
Top guest reviews
Amenities & Room:
the bedroom space was extremely comfortable and the large modern bathroom was terrificpascal added a wonderful personal touch of bottled water in our room and chocolates on the bedthe bed was extremely comfortablethere is access to a lovely well-outfitted kitchenshe's very accommodating everything was hassle free and the bed was so comfortableCleanliness:
the house is beautiful clean and comfortablebeautifully appointed exceedingly clean and comfortable homethe house was very cleanhad a great stay very clean and nicely decoratedit's clean spacious and beautifulHost:
pascale's home is beautiful and she was a wonderful hostsuper host for surepascale was an amazing hostpascale is a great hostshe was very friendly and is an amazing cook tooRead more reviewsLocation:
great location in walking distance to local restaurantscentral location with easy access to restaurants and major highwaysa nice location with lots of restaurants within walking distancebeautiful house at very good locationit's convenient and a great location for my needs
5. Charming artist retreat
Just an hour from NYC, this antique, colonial house still has its original beams. Much of its charm is owed to the traditional furnishings that complement its interior. Guests will have the entire house to themselves. There are four bedrooms, but the couch and sofa bed can also double as comfy sleeping surfaces, bringing the maximum capacity to 10 guests.
There is an outdoor patio with lounge chairs, an umbrella and a grill. If you’re heading out for your fix of fresh air and exercise, Waveny Park is just two blocks away and is great for both hiking and biking.
3.99 km (2.5 mi) from Stamford Museum & Nature Center
6. Upscale cottage in the Silvermine Area
Located in the Silvermine area of New Canaan, this luxurious, upscale home features over 860 square feet (80 square metres) of space. It has its own private driveway and garage, all against a backdrop of well-maintained greenery. This apartment for rent in New Canaan, Connecticut has an open layout, with high ceilings and a large amount of space to spread out. Just around the corner is the Silvermine Art Guild, Silvermine Market and the Gray Barns Restaurant.
8.01 km (5.0 mi) from Stamford Museum & Nature Center
7. Private wing of an elegant home
Guests here will get their own private wing in a large, elegant home. It is essentially a two-bedroom apartment that comes with its own kitchenette. The larger bedroom has a king bed, while the smaller one has a single bed. If needed, there are two additional floor mattresses available.
While its interiors are undoubtedly elegant, it is the house’s surroundings that form the main highlight of this listing. It is surrounded by lush greenery and there is a secluded, private pond, right at the doorstep. In the winter, it looks even more amazing, especially after a snowy night. Quite simply put, this is what a dream home looks like.
New Canaan, Connecticut, United States
5.14 km (3.2 mi) from Stamford Museum & Nature CenterTop guest reviews
Amenities & Room:
beautiful setting lovely roomsthis is a cozy space in a beautiful setting and dorothy is a thoughtful hostbeautiful architectural detail in the master bedroom ceiling space and very good bedCleanliness:
the house is beautiful very clean and privatevery clean with a beautiful pond to sit bythe rooms are comfortable and cleanthe house is very neat clean and comfortable in a quiet & peaceful locationHost:
dorothy is a great host and has a lovely homedorothy was a wonderful hostdorothy was a welcoming hostspectacular property (inside and out) and wonderful hostdorothy has a fantastic home and is a very accommodating hostRead more reviewsLocation:
wonderful stay in a lovely locationquiet and beautiful locationwonderful location and incredible place along the lakethis house is located in a beautiful green quiet neighborhood by a small lakethe private wing of the house was perfect and the location is great
8. Private, lower-level suite on a country lane
Stay right in the heart of New Canaan with this apartment. Guests will have access to the entire lower level of this home. It has a single bedroom with a large king bed. Good for those travelling solo or in twos, the apartment is just minutes from the city’s attractions, like Waveny Park, Grace Farms and the Phillip Johnson Glass House.
Travelling in the winter? Not to worry, the apartment is outfitted with indoor heating. It also has an indoor fireplace that you can get cosy next to, with the clichéd cup of hot chocolate. There is also a firepit outside if you wish to get some fresh air.
New Canaan, Connecticut, United States
6.26 km (3.9 mi) from Stamford Museum & Nature CenterTop guest reviews
Amenities & Room:
i had read reviews and knew this apt would be perfect for an overnight stay while visiting familyit was in a lovely quiet location the king bed extremely comfortable and the amenities excellentsuch a charming and comfortable placeCleanliness:
the space is clean and well organizedvery comfortable and spotless too the rooms are lovely and it is cozy and quietgreat location comfy space very clean and freshHost:
she is a wonderful hosthost was lovelydeborah is a friendly and accommodating hostdeborah is a great host and her accommodations very comfortabledeborah was highly responsive accommodating helpful and very graciousRead more reviewsLocation:
easy location to get aroundgreat location for business in ctbeth cute place for couplesgreat place for a business trip in local areai highly recommend her place if you need a place to stay in the area
9. Private studio and patio near SoNo
This private studio apartment sports dark, modern and artistic décor throughout and is a truly quaint place to stay when visiting the city. It’s close to South Norfolk, where there are many cafes, restaurants and public transportation. Apart from the usual amenities required for a comfortable stay, guests also get to use the bicycle in the apartment, for free. This is particularly useful for exploring the area, such as the harbour.
The door uses a digital lock with a password, which will be shared with guests prior to checking in. This means no worrying about lost keys and anytime-check-ins at guests’ convenience.
Norwalk, Connecticut, United States
10.06 km (6.3 mi) from Stamford Museum & Nature CenterTop guest reviews
Amenities & Room:
staying at melissa’s well appointed guest suite was lovely good closet space spacious bathroom excellent linens and decorcomfy bed nice shower coffee fixings etcmelissa’s place was stylish and comfortablebasement apartment original art is a nice touchroom was exactly what i expected: cozy clean and every listed amenities are providedCleanliness:
great communication with a comfy and clean roomneat and clean placethe space was clean and homeygreat space clean and comfortablemelissa's place was nice clean and affordableHost:
host communicative and gracioushost was easy to communicate with and thoughtfulcozy digs mj’s a great host would definitely returnlots of privacy and tranquility mj was extremely responsive and accommodating as a hostmelissa is a great host i highly recommend this placeRead more reviewsLocation:
good location and neighborhoodvery cute space great location downtowngood location and spacegood neighborhood walking distance to many places15 min walk to great restaurants
Celebrating tradition
From New Canaan’s rich history comes the modern house. While it may sound like another LA or NYC on paper, the city also celebrates tradition, with its many fairs and events. Whether you’re here for business or to explore the city, New Canaan promises to be an event-filled experience.
Frequently asked questions about the top Airbnbs in and near New Canaan, Connecticut
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