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New Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for New Canaan vacation rentals

Smart TV, fireplace, table tennis, computer monitors
Captain's Cottage - Cold Spring Harbor Water Views

Vacation Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is ￥33,839
￥74,828 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Captain's Cottage - Cold Spring Harbor Water Views
Game room
Peaceful apartment on 3.5 acres w/ artist studio.

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ artist studio.
9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is ￥19,671
￥30,233 total
includes taxes & fees
Dec 26 - Dec 27
Peaceful apartment on 3.5 acres w/ artist studio.
1 bedroom, desk, iron/ironing board, free WiFi
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Apartment in Downtown Bridgeport

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
9.6 out of 10, Exceptional, (7)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is ￥21,832
￥35,867 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is ￥30,876
￥74,492 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury Designer 2 bedroom+office/3bed vacation home.
Fridge, microwave, oven, stovetop
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Apartment in Huntington Station

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
10.0 out of 10, Exceptional, (7)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is ￥30,408
￥60,043 total
includes taxes & fees
Jan 7 - Jan 8, 2026
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Vacation Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is ￥17,798
￥38,734 total
includes taxes & fees
Jan 1 - Jan 2, 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Vacation Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
9.8 out of 10, Exceptional, (9)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥27,290
￥54,618 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Cookware/dishes/utensils
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Apartment in Downtown Stamford

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
9.2 out of 10, Wonderful, (11)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥21,754
￥41,781 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds
THE OASIS @ LONG ISLAND

Apartment in Huntington Station

THE OASIS @ LONG ISLAND
10.0 out of 10, Exceptional, (17)
"Place was clean, decorated adorably and well stocked with essentials- even a coffee bar! Communication was also very good. Would definitely recommend! "
United States
natalie m.
The price is ￥38,985
￥73,939 total
includes taxes & fees
Jan 9 - Jan 10, 2026
THE OASIS @ LONG ISLAND
Marina
Seabreeze at the beach west beach Stamford ct.

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (10)
"Excellent property, very clean, nicely furnished. One of the best VRBOs we have rented. Owner was exceptionally good about communication and went out of his way to make sure stay went well. Will come again. "
United States
David S.
The price is ￥26,978
￥64,356 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Seabreeze at the beach west beach Stamford ct.
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is ￥17,525
￥42,697 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is ￥16,210
￥37,803 total
includes taxes & fees
Jan 4 - Jan 5, 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Fridge, microwave, dishwasher, toaster
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Apartment in Port Chester

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
10.0 out of 10, Exceptional, (28)
"10/10 Excellent Ms.Carmen is an amazing host. Prompt communication. Apartment is very clean, private and it had everything we needed. We will ALWAYS stay here when visiting Port Chester. "
United States
Amanda
The price is ￥34,307
￥58,503 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Dining
Luxe Provincial Style Studio w/ Patio & Parking

Apartment in Huntington Station

Luxe Provincial Style Studio w/ Patio & Parking
10.0 out of 10, Exceptional, (3)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is ￥30,408
￥60,043 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxe Provincial Style Studio w/ Patio & Parking
Fridge, microwave, oven, stovetop
Modern Luxe 1BR Apt in Downtown Stamford

Apartment in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥21,076
￥56,945 total
includes taxes & fees
Dec 28 - Dec 29
Modern Luxe 1BR Apt in Downtown Stamford
2 bedrooms, iron/ironing board, WiFi, bed sheets
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Apartment in Downtown Bridgeport

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
The price is ￥38,985
￥59,881 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is ￥16,505
￥43,932 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Renovated 2BR Retreat / Modern Comforts Included
Outdoor dining
Updated, cozy single family in Fairfield County

Vacation Home in Trumbull

Updated, cozy single family in Fairfield County
9.4 out of 10, Exceptional, (12)
"This location is great close to highway and mall."
United States
Sansia D.
The price is ￥43,340
￥85,826 total
includes taxes & fees
Dec 28 - Dec 29
Updated, cozy single family in Fairfield County
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is ￥13,270
￥24,128 total
includes taxes & fees
Dec 28 - Dec 29
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Canaan Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Have stayed here in the past and it has not changed. Has always been good."
Patrick 1-night trip
Posted 4 days ago
Hyatt Regency Greenwich

Find out more about New Canaan

Search for holiday rentals in New Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in New Canaan using one of the methods below:

  • View our selection of featured holiday rentals in New Canaan
  • Use the map to find apartments and other holiday homes in the New Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Canaan while they last

Look no further and take a look at our great range of rental properties in New Canaan!

Frequently asked questions

Can I find a vacation rental in New Canaan?

Yes, you can find vacation rentals in New Canaan near Goldenberry, or you can go with a secluded option if you want a relaxing stay. New Canaan is known for its seafood restaurants.

What are some of the best vacation rentals that New Canaan has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: Visitors like this New Canaan vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in New Canaan?

With 6 Expedia vacation rentals, you're sure to find just the right place for your New Canaan stay.

What can I see and do in New Canaan?

Cultural attractions include The Glass House and Silvermine Arts Center, whereas Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Glass House Visitor's Center are other places to visit while you're in town.

What are vacation rentals like in New Canaan?

Vacation rentals are private accommodations you can book for a couple days or more in New Canaan. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.