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New Canaan Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in New Canaan

Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (73)
"It was great"
United States
Natalie
The price is HK$945
HK$1,086 total
includes taxes & fees
19 Nov - 20 Nov
Stamford Suites
Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$1,865
HK$2,145 total
includes taxes & fees
20 Nov - 21 Nov
Guesthouse at Norwalk Inn
Reception
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is HK$714
HK$1,722 total
includes taxes & fees
25 Nov - 26 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Pool
Business or Weekend escape

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$622
HK$1,094 total
includes taxes & fees
23 Nov - 24 Nov
Business or Weekend escape
Front of property
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is HK$5,430
HK$8,965 total
includes taxes & fees
19 Nov - 20 Nov
Beechmont - Perfect for Family Retreat!
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, (4)
"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$5,597
HK$10,746 total
includes taxes & fees
20 Nov - 21 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Smart TV
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Scarsdale
9.0 out of 10, Wonderful, (4)
"Space was clean, nice, and hosts were very helpful and communicative."
United States
Steven C.
The price is HK$1,321
HK$2,534 total
includes taxes & fees
23 Nov - 24 Nov
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
1 bedroom, iron/ironing board, free WiFi, bed sheets
Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

White Plains
10.0 out of 10, Exceptional, (1)
"This location was tranquil and close to everything I expected for meals and entertainment. Easy to get to and felt warm and inviting. Fayeem was responsive and helpful towards my requests. I look forward to staying here again. Thank you!"
United States
Moses A.
Elegant Hideaway • Free Parking
Private kitchen
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4.0 star property
White Plains
8.0 out of 10, Very good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is HK$1,826
HK$2,858 total
includes taxes & fees
19 Nov - 20 Nov
Luxury NY Home with Free Parking
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is HK$3,736
HK$5,766 total
includes taxes & fees
20 Nov - 21 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.
1 bedroom, desk, iron/ironing board, free WiFi
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, (1)
The price is HK$661
HK$1,273 total
includes taxes & fees
20 Nov - 21 Nov
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Property grounds
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)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is HK$978
HK$3,037 total
includes taxes & fees
19 Nov - 20 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
Property grounds
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport
9.4 out of 10, Exceptional, (13)
"All went well. Owners live in cottage on property. The bay is gorgeous."
United States
Rob M.
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Fridge, microwave, stovetop, dishwasher
Charming Home in Seaside

Charming Home in Seaside

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"Amazing beautiful property in a rustic urban environment. Perfect check in, super comfortable, TVs in every room… essentially a new house. Close to the water and amphitheater. If you’re used to city life we’d recommend it, because we are!"
United States
Matt H.
Charming Home in Seaside
Interior
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)
"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$933
HK$1,530 total
includes taxes & fees
20 Nov - 21 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Marina
Comfy cozy 2-bedroom apartment in great location in Mamaroneck NY near NYC

Comfy cozy 2-bedroom apartment in great location in Mamaroneck NY near NYC

2.0 star property
Mamaroneck
Comfy cozy 2-bedroom apartment in great location in Mamaroneck NY near NYC
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

Trumbull Marriott Shelton

Trumbull Marriott Shelton

10/10 Excellent
"All was good - polite staff, clean room, comfortable beds."
philip 1-night trip
Posted 3 days ago
Trumbull Marriott Shelton

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!

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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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday home rental outside of New Canaan 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 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 New Canaan Museum & Historical Society, whereas God's Acre and Mead Memorial Park are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and New Canaan Historical Society 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.