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Vacation rentals in New Canaan

Vacation rentals in New Canaan

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in New Canaan

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Adirondacks in Westchester
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1.5 baths
    Adirondacks in Westchester

    Located on quiet, private 5.5 acre estate with swimmable lake, fantastic landscape. Complete privacy, like being in the Adirondacks, but just one hour from NYC. Cottage has high end appliances (Sub-Zero, Miele) with separate road and entrance. Perfect for a getaway from NYC and easily accessible by car or train (Stamford station). Can be combined with Adirondacks in Westchester 2 to provide an additional bedroom in a separate building to accommodate a total of four guests. Excellent wifi.

    What guests are saying:

    “Beautiful home in harmony with nature, spectacular view from every room, incredible porch, close to lots of great dining and other options. We loved eating at the Kitchen Table for breakfast and Lucia's for dinner, both less than 20 minutes away.”

  • Mid Century Modern Cottage
    Entire house · 2 guests · 1 bed · 1 bath
    Mid Century Modern Cottage

    Mid Century Modern home in the middle of Fairfield County.

    What guests are saying:

    “This cottage is just wonderful. The description and photos show you exactly what you're gonna get. It's not huge, but it's wonderfully cozy and quiet--feels like a true getaway the moment you walk in, and there's a lovely view of trees off a nice, private deck. The bed loft is terrifically cozy, and I slept like a baby here--not a sound all night. It was quite cold outside during my stay, but the heat was fabulous in the cottage. And Paul's wife baked some delicious brownies that were waiting upon my arrival; I'm not even a dessert person, but I couldn't resist, as they were so good. Paul was also extremely attentive. The check-in was seamless, and he answered my texted questions both before and during my stay immediately. If you're looking for cozy, rustic value and a true get-away-from-it-all stay, this is the place for you!”

  • Huckleberry Quarters, the Cozy Redding Retreat.
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Huckleberry Quarters, the Cozy Redding Retreat.

    Huckleberry Quarters, totally renovated-2015 studio apartment in secluded, 1918 farm house. Nature lovers retreat within hiking distance of the Saugatuck reservoir. Private entrance with all the amenities; internet, access to laundry. Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

    What guests are saying:

    “My wife and I can’t wait to come back; never knew I wanted to stay in the middle of Connecticut in the woods until I stayed at The Huckleberry House. Lol I’ll start by saying that we are used to staying in modern hotels and when I wanted to get away during a pandemic - Connecticut was the closest state to NY that had restaurants open and no masks, so we decided he’ll, let’s do it - and WE ARE SO HAPPY WE DID! We arrived and were greeted by the 5 amazing dogs that live on property as well as by the owners (Best greeting ever). William was available by text the entire stay if we needed anything but they also allowed us space and privacy as well. The cottage was designed with the most thoughtful of touches. Every single thing you could ever need was provided, literally. They even provided FRESH eggs, cream, oh and bread. They truly thought about every detail of someone being comfortable and feeling cared for. The huckleberry house made me feel like I was a kid again. Walking in nature without a care in the world and sunsets to die for. The local foodie spots were equally as delicious (Try: Wire Mill bbq and The Barn Door (best Penne ala vodka ever!). Over all it was the reset our marriage and life needed, were so thankful to William and his husband for the experience. ❤️”

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Popular amenities for New Canaan vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in New Canaan

Weekend Retreat
SUPERHOSTEntire house
Weekend Retreat
Price:$203 CAD/night
Beautiful Private Entrance ensuite in Fairfield
Entire guest suite
Beautiful Private Entrance ensuite in Fairfield
Price:$60 CAD/night
WELCOME TO NEW ENGLAND. (Upstairs room 2)
SUPERHOSTPrivate room
WELCOME TO NEW ENGLAND. (Upstairs room 2)
Price:$67 CAD/night
☆Charming Studio - Private/Self Check-In/Parking☆
Entire guest suite
☆Charming Studio - Private/Self Check-In/Parking☆
Price:$82 CAD/night
Work from home, private room  and king bed
SUPERHOSTPrivate room
Work from home, private room and king bed
Price:$61 CAD/night
Private small studio Near Harbor Point
SUPERHOSTPrivate room
Private small studio Near Harbor Point
Price:$71 CAD/night
Charming Fairfield Cottage By The Sea
SUPERHOSTEntire house
Charming Fairfield Cottage By The Sea
Price:$272 CAD/night
Comfortable Colonial Urban retreat.
SUPERHOSTEntire guest suite
Comfortable Colonial Urban retreat.
Price:$102 CAD/night
Charming Greenwich studio, 0.2 miles from train
SUPERHOSTEntire guest suite
Charming Greenwich studio, 0.2 miles from train
Price:$157 CAD/night
Private Room by Fairfield Metro Station
Private room
Private Room by Fairfield Metro Station
Price:$52 CAD/night
Luxurious Barn With New England Charm
SUPERHOSTEntire house
Luxurious Barn With New England Charm
Price:$176 CAD/night
Gem by the Sound
SUPERHOSTEntire house
Gem by the Sound
Price:$340 CAD/night
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