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New Canaan Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for New Canaan holiday rentals

Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is HK$2,463
HK$5,652 total
includes taxes & fees
22 Jul - 23 Jul
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is HK$784
HK$1,444 total
includes taxes & fees
11 Jul - 12 Jul
Welcome to Sweet Abby Rose!
1 bedroom, desk, iron/ironing board, free WiFi

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is HK$855
HK$1,508 total
includes taxes & fees
13 Jul - 14 Jul
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
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, (98 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is HK$1,430
HK$2,123 total
includes taxes & fees
4 Aug - 5 Aug
DUNE Fairfield Beach
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is HK$1,623
HK$2,674 total
includes taxes & fees
15 Jul - 16 Jul
Elite room stay
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (55 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is HK$666
HK$1,149 total
includes taxes & fees
13 Jul - 14 Jul
Business or Weekend escape
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is HK$1,058
HK$2,324 total
includes taxes & fees
13 Jul - 14 Jul
Zen, Spacious & Comfy 2 bed, Lux beds
Smart TV

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is HK$939
HK$2,556 total
includes taxes & fees
27 Jul - 28 Jul
Stamford Hideaway w/ Fire Pit
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (32 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,725
HK$3,282 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
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, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveller
The price is HK$1,168
HK$2,653 total
includes taxes & fees
15 Jul - 16 Jul
Renovated 2BR Retreat / Modern Comforts Included
Smart TV

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.2 out of 10, Good, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is HK$1,235
HK$2,098 total
includes taxes & fees
16 Jul - 17 Jul
Centric property close to all the great things in the city
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,952
HK$3,523 total
includes taxes & fees
30 Jul - 31 Jul
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (41 reviews)
"Room was great for the price and the host was a pleasure to deal with. "
United States
steven l.
The price is HK$1,482
HK$2,715 total
includes taxes & fees
14 Jul - 15 Jul
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is HK$1,176
HK$2,107 total
includes taxes & fees
8 Aug - 9 Aug
The Tipsy Gypsy - Studio Apartment
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, (92 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is HK$1,402
HK$2,787 total
includes taxes & fees
23 Jul - 24 Jul
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"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 HK$1,529
HK$3,010 total
includes taxes & fees
14 Jul - 15 Jul
Luxe Provincial Style Studio w/ Patio & Parking
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is HK$1,607
HK$3,108 total
includes taxes & fees
14 Jul - 15 Jul
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is HK$1,129
HK$2,412 total
includes taxes & fees
20 Jul - 21 Jul
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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
9.4 out of 10, Exceptional, (8 reviews)
"Nice little spot with a great host."
United States
J M.
The price is HK$784
HK$1,419 total
includes taxes & fees
13 Jul - 14 Jul
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
1 bedroom, desk, iron/ironing board, free WiFi

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is HK$1,098
HK$1,803 total
includes taxes & fees
15 Jul - 16 Jul
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
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

Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"I enjoyed my stay down to the pool but is far from the main museums"
Willie 2-night trip
Posted less than an hour ago
Sonesta White Plains Downtown

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 holiday rental in New Canaan?

Yes, there are holiday rentals in New Canaan close to Silvermine Arts Center, 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, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: 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 4 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 Historical Society, whereas Old Stamford Road Bird Sanctuary and Mead Memorial Park 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.