Places to stay in New Canaan

Book unique places to stay, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for New Canaan places to stay

Other great vacation rentals in New Canaan

Top guest favorite
Treehouse in Wallkill
4.99 out of 5 average rating, 311 reviews

The Treecastle at the Roundhouse Homestead

NicoleRating, 5 stars6 days ago
The treehouse was such an amazing stay for us. Everything was clean, the host was super responsive and helpful, and the location was good too. We felt right at home staying here & will absolutely be back. I wish we could have spent more time here. The outdoor bathroom was one of my favorite parts. There was overall a peaceful atmosphere and was a great way place relax and unwind. The hosts left us some delicious homemade bread and muffins. They also included fresh honey and eggs. They put so much love and thought into every detail of the treehouse, surrounding area and even the guestbook. I highly recommend booking - you won’t regret it!!
Guest favorite
Home in West Norwalk
4.96 out of 5 average rating, 50 reviews

Modern Nature Retreat

MarkRating, 5 stars5 months ago
Beautiful house, great place for a relaxing weekend
Top guest favorite
Home in Norwalk
5 out of 5 average rating, 54 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

DennyseRating, 5 stars4 days 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 favorite
Apartment in Wall Street
5 out of 5 average rating, 63 reviews

Phoenix Engine #1

GrantRating, 5 stars3 weeks ago
Nathan’s a great host and he provided a great welcome pack. Great home for my wife and I and adult son. Plenty of space and walkable to coffee shops and river. Awesome communication and offered a very helpful relaxed late check out at no cost. Totally recommend this host and this property
Top guest favorite
Guesthouse in Waccabuc
4.99 out of 5 average rating, 94 reviews

French Guest House in Waccabuc

KikoRating, 5 stars1 week ago
Beautiful place! Very tranquil, wish we stayed for longer because the room was filled with books I would have loved to read :)
Superhost
Home in Darien
4.81 out of 5 average rating, 203 reviews

Convenient and Cozy Antique Cape

JonRating, 5 stars3 weeks ago
The home was dated, but definitely worth the price. Convenient to shopping (Trader Joe's), access to I95, and just a short drive to downtown Darien. The amenities are also dated, i.e., not a walk-in shower but a jacuzzi type tub. Rory's restaurant was next door, which had very good food and reasonably priced. The host needs to add hand towels for the bathroom, and tea towels for the kitchen. The host was very responsive to text messages. Overall, we very much enjoyed the house.
Superhost
Guesthouse in Wilton
4.98 out of 5 average rating, 44 reviews

The Ciderhouse Cottage - private escape in Wilton

OdalysRating, 5 stars5 days ago
We loved our stay at this beautiful private cottage! It was perfect for our long weekend getaway since we were in the area for a wedding and grad celebration. Very clean, tidy, and spacious—plenty of room to get ready!
Guest favorite
Home in Pound Ridge
4.96 out of 5 average rating, 23 reviews

Chic Midcentury Retreat with Private Pond near NYC

JasonRating, 5 stars2 weeks ago
This is an exceptional home. Elegantly designed, beautifully decorated, in a secluded location. Intimate but with plenty of space for a family to stay. The owners were responsive and informative. 12 out of 10 stars.

Quick stats about vacation rentals in New Canaan

  • Total rentals

    40 properties

  • Total number of reviews

    930 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

Frequently Asked Questions

  • Where should I stay in New Canaan?

    Make yourself at home in New Canaan by choosing from our most frequently booked neighborhoods. We have over 240 vacation rentals in West Norwalk, and over 110 vacation rentals in Silvermine.

  • Are there vacation rentals with a dedicated workspace in New Canaan?

    Yes! Work meets play with ease at over 30 vacation rentals in New Canaan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in New Canaan?

    Four-legged friends are welcome in New Canaan. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in New Canaan have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in New Canaan. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore