New Canaan places to stay

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

Top-rated places to stay in New Canaan

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Stamford
Sugar Shack Studio | Downtown Skyline Views
Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!
Feb 14 – 21
$121 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Guest suite in Fairfield
Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen
Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.
Oct 5 – 12
$99 per night
4.92 out of 5 average rating, 109 reviews
Superhost
Apartment in Stamford
Sunset Retreat: 1BR Walking Distance to the Beach
Welcome to our charming and spacious 1 bedroom Airbnb in the heart of the beach district in Stamford! This delightful 1st fl apartment offers everything you need for a memorable stay. Prime location offers the best of both worlds. Just a short 5-min stroll will take you to the local train station, providing easy access to neighboring cities and attractions. Additionally, downtown Stamford is a mere 7-min drive, where you can indulge in a wide array of dining, shopping, and entertainment options.
Dec 30 – Jan 6
$100 per night
4.82 out of 5 average rating, 142 reviews

Popular amenities for New Canaan places to stay

Stay near New Canaan's top sights

Grace Farms31 locals recommend
The Glass House27 locals recommend
Waveny Park12 locals recommend
Stamford Museum & Nature Center26 locals recommend
The Market at Pound Ridge Square6 locals recommend
South End3 locals recommend

Other great vacation rentals in New Canaan

Guest favorite
Apartment in Westport
Spacious Westport Apt surrounded by nature
Nov 13 – 20
$155 per night
4.94 out of 5 average rating, 109 reviews
Guest favorite
Cottage in Pound Ridge
Adirondacks in Westchester
Jan 10 – 17
$203 per night
4.93 out of 5 average rating, 168 reviews
Guest favorite
Guest suite in Bedford
Sweet Suite in walkable historic Bedford Village
Sep 6 – 13
$148 per night
4.96 out of 5 average rating, 122 reviews
Guest favorite
Guest suite in Bayville
Romantic, Cozy and Private, 1 Block from Beach
Dec 26 – Jan 2
$74 per night
4.92 out of 5 average rating, 417 reviews
Guest favorite
Apartment in Brookfield
Peaceful apartment on 3.5 acres w/ Artist studio.
Dec 8 – 15
$129 per night
4.94 out of 5 average rating, 178 reviews
Superhost
Apartment in Westport
Spacious Upscale Studio with Pool Table
May 26 – Jun 2
$118 per night
4.85 out of 5 average rating, 144 reviews
Guest favorite
Apartment in Norwalk
The Seasons Luxe Pad 1 Bedroom | Center of Norwalk
Jul 9 – 16
$98 per night
4.91 out of 5 average rating, 293 reviews
Guest favorite
Home in Pound Ridge
Peaceful Light-Filled Guesthouse 1 Hour From NYC
Nov 11 – 18
$598 per night
5.0 out of 5 average rating, 122 reviews
Guest favorite
Guest suite in Wilton
Guest suite with private enter
Apr 16 – 23
$83 per night
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Norwalk
❤️ Your Silvermine Hideaway, nestled in nature.
Nov 15 – 22
$176 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Apartment in Stamford
Standalone Cottage surrounded by woods
Dec 22 – 29
$88 per night
5.0 out of 5 average rating, 46 reviews
Guest favorite
Guesthouse in Wilton
The Cozy Little Cottage
Apr 30 – May 7
$123 per night
4.96 out of 5 average rating, 94 reviews

Other great vacation rentals in New Canaan

Guest favorite
Apartment in Norwalk
S. Norwalk Apt near the water!
Jun 3 – 10
$138 per night
5.0 out of 5 average rating, 29 reviews
Guest favorite
Apartment in Stamford
Stamford’s Island Inspired Efficiency
Sep 17 – 24
$76 per night
4.87 out of 5 average rating, 38 reviews
Guest favorite
Cottage in Weston
The River Loft
Jun 27 – Jul 4
$325 per night
4.96 out of 5 average rating, 28 reviews
Guest favorite
Home in Wilton
The Yellow House
Aug 14 – 21
$598 per night
4.98 out of 5 average rating, 51 reviews
Guest favorite
Home in Pound Ridge
Private farm cottage +hiking
Sep 6 – 13
$180 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Home in Norwalk
Modern Nature Retreat
Nov 18 – 25
$840 per night
4.94 out of 5 average rating, 34 reviews
Guest favorite
Guesthouse in Wilton
The Ciderhouse Cottage - private escape in Wilton
Aug 18 – 25
$286 per night
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Norwalk
The Pond House 3 bed 2 bath hot tub sauna and more
Apr 14 – 21
$360 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Guesthouse in Pound Ridge
A Lovely Cottage in the Woods
Apr 5 – 12
$206 per night
4.95 out of 5 average rating, 58 reviews
Guest favorite
Home in Bedford
Exquisite Bedford Lux Retreat.
Dec 9 – 16
$518 per night
4.93 out of 5 average rating, 27 reviews
Guest favorite
Apartment in Norwalk
Private Studio In Coastal Rowayton!
Aug 3 – 10
$166 per night
4.95 out of 5 average rating, 40 reviews
Guest favorite
Guesthouse in Bedford
Red Coat Cottage
Dec 5 – 12
$266 per night
5.0 out of 5 average rating, 12 reviews

Quick stats about vacation rentals in New Canaan

Total rentals

50 properties

Wifi availability

50 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

950 reviews

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 house rentals with a dedicated workspace in New Canaan?

    Yes! Work meets play with ease at over 10 house rentals in New Canaan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in New Canaan?

    New Canaan has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in New Canaan have wifi?

    Absolutely! We offer over 30 house rentals with wifi in New Canaan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in New Canaan have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in New Canaan. Enjoy a tailored experience with all the comforts you desire.

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

    Four-legged friends are welcome in New Canaan. Choose from more than 10 house 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.

  • What are the most popular amenities for House Rentals in New Canaan?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore