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

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

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 25 – Nov 1

G$23,894 GYD per night
Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 205 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Jul 18 – 25

G$25,794 GYD per night
Guest favorite

Guesthouse in Norwalk

5.0 out of 5 average rating, 110 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

May 1 – 8

G$70,848 GYD per night

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
South End3 locals recommend
The Market at Pound Ridge Square6 locals recommend

Other great vacation rentals in New Canaan

Guest favorite

Apartment in Westport

4.94 out of 5 average rating, 112 reviews

Spacious Westport Apt surrounded by nature

Jan 12 – 19

G$37,061 GYD per night
Guest favorite

Place to stay in Westport

4.96 out of 5 average rating, 276 reviews

Sunny Westport 2 BR Retreat above Historic Mill

Jan 26 – Feb 2

G$36,807 GYD per night
Guest favorite

Cottage in Pound Ridge

4.93 out of 5 average rating, 168 reviews

Adirondacks in Westchester

Jun 22 – 29

G$48,598 GYD per night
Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 104 reviews

Sunny Lakeview Guesthouse

Dec 14 – 21

G$26,889 GYD per night
Guest favorite

Guest suite in Bayville

4.92 out of 5 average rating, 420 reviews

Romantic, Cozy and Private, 1 Block from Beach

Feb 25 – Mar 4

G$17,800 GYD per night
Guest favorite

Apartment in Northport

4.92 out of 5 average rating, 126 reviews

Harbor Studio - Across from historic Northport doc

Mar 19 – 26

G$26,699 GYD per night
Guest favorite

Guesthouse in Fairfield

4.96 out of 5 average rating, 170 reviews

Southport, CT across from BEACH

Mar 11 – 18

G$55,664 GYD per night
Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 24 reviews

Guest suite with private enter

Apr 30 – May 7

G$19,662 GYD per night
Guest favorite

Home in Norwalk

5.0 out of 5 average rating, 33 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

Nov 17 – 24

G$42,617 GYD per night
Guest favorite

Apartment in Stamford

5.0 out of 5 average rating, 49 reviews

Standalone Cottage surrounded by woods

Oct 8 – 15

G$22,806 GYD per night
Guest favorite

Guest suite in Stamford

4.97 out of 5 average rating, 35 reviews

Retreat in North Stamford

Jul 31 – Aug 7

G$29,631 GYD per night
Guest favorite

Apartment in Norwalk

5.0 out of 5 average rating, 30 reviews

S. Norwalk Apt near the water!

Apr 2 – 9

G$29,769 GYD per night

Other great vacation rentals in New Canaan

Guest favorite

Cottage in Weston

4.97 out of 5 average rating, 29 reviews

The River Loft

Jun 27 – Jul 4

G$77,288 GYD per night
Guest favorite

Home in Norwalk

4.94 out of 5 average rating, 34 reviews

Modern Nature Retreat

Nov 21 – 28

G$202,783 GYD per night
Guest favorite

Home in Wilton

4.98 out of 5 average rating, 51 reviews

The Yellow House

Aug 27 – Sep 3

G$144,157 GYD per night
Guest favorite

Cottage in Norwalk

4.92 out of 5 average rating, 38 reviews

Charming Coastal Retreat: 2BR Cottage, Rustic Char

Jan 20 – 27

G$32,034 GYD per night
Guest favorite

Guesthouse in Pound Ridge

4.95 out of 5 average rating, 60 reviews

A Lovely Cottage in the Woods

Apr 19 – 26

G$49,531 GYD per night
Guest favorite

Home in Norwalk

5.0 out of 5 average rating, 21 reviews

The Pond House 3 bed 2 bath hot tub sauna and more

Apr 13 – 20

G$89,928 GYD per night
Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 17 reviews

Private farm cottage +hiking

Jun 15 – 22

G$43,433 GYD per night
Guest favorite

Guesthouse in Wilton

5.0 out of 5 average rating, 21 reviews

The Ciderhouse Cottage - private escape in Wilton

Aug 27 – Sep 3

G$68,938 GYD per night
Guest favorite

Apartment in Norwalk

4.95 out of 5 average rating, 40 reviews

Private Studio In Coastal Rowayton!

Jul 5 – 12

G$40,374 GYD per night
Guest favorite

Apartment in Stamford

4.87 out of 5 average rating, 39 reviews

Stamford’s Island Inspired Efficiency

Oct 12 – 19

G$19,015 GYD per night
Guest favorite

Home in Westport

5.0 out of 5 average rating, 6 reviews

Farmhouse 1899: Westport, CT

Apr 4 – 11

G$144,185 GYD per night
Guest favorite

Home in Bedford

5.0 out of 5 average rating, 17 reviews

The Waterside Guest House with Pool & Tennis, Golf

Oct 4 – 11

G$204,823 GYD per night

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 110 vacation rentals in Silvermine, and over 240 vacation rentals in West Norwalk.

  • 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