Top 9 Airbnb Vacation Rentals In And Near New Canaan, Connecticut - Updated 2022

airbnb New-Canaan CT

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.

1. Rustic cottage getaway (from USD 136)

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.

NY Rustic Cottage Getaway
Mount Kisco, New York, United States
473 reviews Superhost  Wifi Available
Barn 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the cabin has a gorgeous view and is extremely spacious yet cozy
beautiful space very comfortable and cosy
i appreciated the small touches such as leaving coffee ready for us at the kitchen
comfortable creative and calming we will definitely return
i came expecting a cabin but this is truly a luxurious cottage getaway cozy and inspired
everything was very clean and full of thoughtful touches
it was sparkling clean and the house has everything you need
you can tell she created her space with tlc - clean with beautiful art and comfortable vibes
nina was a wonderful host she was very responsive and warm
nina was a sweet and thoughtful host
nina was an amazing host & enjoyed chatting with her
nina was a great host and we recommend visiting her space
nina is an amazing host
close to some great restaurants
it’s located extremely close to the train station which makes taking an uber super cheap
good location to visit blue hill at stone barns
close to great hikes sculpture gardens and town is nearby
nina's house is a perfect place to getaway from a busy city
Read more reviews

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.

Charming Private Room in Sea Captain House (#2)
Norwalk, Connecticut, United States
158 reviews Superhost  Wifi Available
Private room in home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
i loved the furnishings in the room
i highly recommend it to all even those skeptical of sharing a bathroom and kitchen
the room was large and comfortable
the room (#2) was spacious and beautiful
the bed was quite comfortable as well
the room was clean and the bed was comfortable
clean quiet welcoming original and very comfortable
the room and bathroom were extremely clean
communication was a breeze and the house was tidy and pleasant
a beautiful quiet house clean comfortable rooms convenient location
wonderful host and beautiful place
also the owner is very flexible and friendly
friendly host cute and cozy home
beautiful home and host was very nice
first of all the host was very friendly and conversational
the location in norwalk was perfect
this place is amazing it's well located in norwalk walking distance from the beach
nice place to stay in a convenient location
easy to get to from the train station (we didn't have a car)
beautiful low-key neighborhood close to rowayton and sono
Read more reviews

3. Historical, mid-century modern, Zen home (from USD 425)

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.

Unique Midcentury Zen House sculptor studio in CT
Stamford, Connecticut, United States
180 reviews Superhost  Wifi Available
Entire home 1 Bed 2 Guests 1 Bedroom 2 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
the area around it has comfortable beach chairs and lounge chairs
her place is wonderfully comfortable serene and artful we felt so lucky to be there
i would certainly stay with her again especially in the warmer months when her pool is open
great facility - olga is excelleny
the pool is outrageously beautiful and the space is just so perfect
there were many clean towels in the bathroom
everything was so clean and neat
the place is unique clean and very relaxing
the pool was super clean and we had all to ourselves
the space itself is very clean and stocked with everything you might need during a stay
olga was a fantastic host
olga is an amazing host
olga is a great host
olga is a great host
olga is an awesome host
i highly recommend this location
a delightfully close out of nyc get away
it seemed to close for comfort to me
still close enough to stamford to create a convenient holiday
i would highly recommend this location
Read more reviews

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.

Sunny Room in charming 1920 house
Norwalk, Connecticut, United States
157 reviews  Wifi Available
Private room in home 1 Bed 2 Guests 1 Bedroom 1 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
the bedroom space was extremely comfortable and the large modern bathroom was terrific
pascal added a wonderful personal touch of bottled water in our room and chocolates on the bed
the bed was extremely comfortable
there is access to a lovely well-outfitted kitchen
she's very accommodating everything was hassle free and the bed was so comfortable
the house is beautiful clean and comfortable
beautifully appointed exceedingly clean and comfortable home
the house was very clean
had a great stay very clean and nicely decorated
it's clean spacious and beautiful
pascale's home is beautiful and she was a wonderful host
super host for sure
pascale was an amazing host
pascale is a great host
she was very friendly and is an amazing cook too
great location in walking distance to local restaurants
central location with easy access to restaurants and major highways
a nice location with lots of restaurants within walking distance
beautiful house at very good location
it's convenient and a great location for my needs
Read more reviews

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.

Charming Artist Retreat NYC/Skiing/Nature/Trails
42 reviews
Entire house 5 Beds 12 Guests

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.

Private Upscale Cottage, historic Silvermine area
7 reviews
Guesthouse 1 Bed 2 Guests

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.

Private wing of elegant home on secluded pond, CT
New Canaan, Connecticut, United States
61 reviews
Entire guest suite 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
beautiful setting lovely rooms
this is a cozy space in a beautiful setting and dorothy is a thoughtful host
beautiful architectural detail in the master bedroom ceiling space and very good bed
the house is beautiful very clean and private
very clean with a beautiful pond to sit by
the rooms are comfortable and clean
the house is very neat clean and comfortable in a quiet & peaceful location
dorothy is a great host and has a lovely home
dorothy was a wonderful host
dorothy was a welcoming host
spectacular property (inside and out) and wonderful host
dorothy has a fantastic home and is a very accommodating host
wonderful stay in a lovely location
quiet and beautiful location
wonderful location and incredible place along the lake
this house is located in a beautiful green quiet neighborhood by a small lake
the private wing of the house was perfect and the location is great
Read more reviews

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.

Private Lower Level on CT Country Lane~BRIGHTSIDE~
New Canaan, Connecticut, United States
35 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
i had read reviews and knew this apt would be perfect for an overnight stay while visiting family
it was in a lovely quiet location the king bed extremely comfortable and the amenities excellent
such a charming and comfortable place
the space is clean and well organized
very comfortable and spotless too the rooms are lovely and it is cozy and quiet
great location comfy space very clean and fresh
she is a wonderful host
host was lovely
deborah is a friendly and accommodating host
deborah is a great host and her accommodations very comfortable
deborah was highly responsive accommodating helpful and very gracious
easy location to get around
great location for business in ct
beth cute place for couples
great place for a business trip in local area
i highly recommend her place if you need a place to stay in the area
Read more reviews

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.

Modern Design & PRIVATE Studio & PATIO near SONO
Norwalk, Connecticut, United States
192 reviews
Entire house 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
staying at melissa’s well appointed guest suite was lovely good closet space spacious bathroom excellent linens and decor
comfy bed nice shower coffee fixings etc
melissa’s place was stylish and comfortable
basement apartment original art is a nice touch
room was exactly what i expected: cozy clean and every listed amenities are provided
great communication with a comfy and clean room
neat and clean place
the space was clean and homey
great space clean and comfortable
melissa's place was nice clean and affordable
host communicative and gracious
host was easy to communicate with and thoughtful
cozy digs mj’s a great host would definitely return
lots of privacy and tranquility mj was extremely responsive and accommodating as a host
melissa is a great host i highly recommend this place
good location and neighborhood
very cute space great location downtown
good location and space
good neighborhood walking distance to many places
15 min walk to great restaurants
Read more reviews

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

1. Which Airbnbs in and near New Canaan have parking?

Driving to New Canaan? You need not worry about parking space as most of the accommodation options here offer free parking within the premises including this sunny room in a charming 1920s house, this historical, mid-century modern, Zen home, and this charming private room in a sea captain’s house.

2. Which Airbnbs in and near New Canaan have WiFi access?

For most travelers, WiFi access is one of the most sought-out features when it comes to choosing an accommodation. Good thing all of the Airbnbs here offer free WiFi access including this rustic cottage getaway, this charming private room in a sea captain’s house, and this historical, mid-century modern, Zen home.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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