New Canaan Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for New Canaan holiday rentals

Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Fridge, microwave, oven, stovetop

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$827
HK$2,271 total
includes taxes & fees
13 Feb - 14 Feb
Renovated 2BR Retreat / Modern Comforts Included
Terrace/patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is HK$970
HK$2,468 total
includes taxes & fees
10 Feb - 11 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Interior

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"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 HK$1,058
HK$3,154 total
includes taxes & fees
10 Feb - 11 Feb
Luxury Designer 2 bedroom+office/3bed vacation home.
2 bedrooms, iron/ironing board, travel cot, WiFi

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is HK$827
HK$2,256 total
includes taxes & fees
10 Feb - 11 Feb
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Interior

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is HK$953
HK$1,620 total
includes taxes & fees
10 Feb - 11 Feb
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$2,749
HK$3,162 total
includes taxes & fees
27 Feb - 28 Feb
Guesthouse at Norwalk Inn
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (98 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
The price is HK$1,019
HK$1,172 total
includes taxes & fees
23 Feb - 24 Feb
Stamford Suites
Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$859
HK$2,147 total
includes taxes & fees
10 Feb - 11 Feb
Elegant Hideaway with Free Parking
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay here. The rooms are clean and comfortable. The hosts are very friendly and hospitable."
United States
Joseph M.
The price is HK$883
HK$1,930 total
includes taxes & fees
10 Feb - 11 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, microwave, oven, stovetop

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is HK$2,532
HK$5,798 total
includes taxes & fees
10 Feb - 11 Feb
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Fridge, microwave, oven, stovetop

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful "
United States
Nolufefe Z.
The price is HK$1,131
HK$2,879 total
includes taxes & fees
11 Feb - 12 Feb
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Exterior

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
9.6 out of 10, Exceptional, (8 reviews)
"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "
United States
Nancy H.
The price is HK$6,094
HK$11,411 total
includes taxes & fees
10 Feb - 11 Feb
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90 reviews)
"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 HK$937
HK$2,215 total
includes taxes & fees
10 Feb - 11 Feb
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Beach

Cozy Cottage with Fire Pit, near Beach

Cozy Cottage with Fire Pit, near Beach
Fairfield
10.0 out of 10, Exceptional, (27 reviews)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is HK$1,399
HK$3,827 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Cottage with Fire Pit, near Beach
Marina

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is HK$1,578
HK$3,633 total
includes taxes & fees
10 Feb - 11 Feb
Captain's Cottage - Cold Spring Harbor Water Views
1 bedroom, iron/ironing board, free WiFi, bed sheets

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2 reviews)
"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 HK$938
HK$1,538 total
includes taxes & fees
10 Feb - 11 Feb
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$930
HK$2,228 total
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking
Fridge, microwave, oven, stovetop

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is HK$1,135
HK$3,101 total
includes taxes & fees
10 Feb - 11 Feb
Marine Theme - 4 BR - Backyard - Fire pit
Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is HK$4,297
HK$6,079 total
includes taxes & fees
10 Feb - 11 Feb
Luxury NYC Home Game Room Free Parking
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

J House Greenwich

J House Greenwich

10/10 Excellent
"Room was immaculate with fabulous amenities. Staff was friendly and helpful. Great proximity to Greenwich Ave and Capitol Theater. 10/10"
Michael 1-night trip
Posted 1 day ago
J House 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
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  • 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!

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Frequently asked questions

Can I find a holiday rental in New Canaan?

Yes, there are holiday rentals in New Canaan close to Goldenberry, or you can select a more secluded option if you're looking for a relaxing stay. New Canaan is known for its seafood restaurants.

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

Captain's Cottage - Cold Spring Harbor Water Views: This holiday home rental outside of New Canaan is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals will I find in New Canaan?

With 6 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in New Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Canaan. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.