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New Canaan Holiday Rentals

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Our top choices for New Canaan holiday rentals

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 NZ$1,269
includes taxes & fees
30 June - 1 July
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

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 NZ$402
includes taxes & fees
12 July - 13 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is NZ$486
includes taxes & fees
27 July - 28 July
DUNE Fairfield Beach

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is NZ$547
includes taxes & fees
29 June - 30 June
Welcoming 1 bedroom apartment in beautiful harbor village.

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 NZ$260
includes taxes & fees
29 June - 30 June
Business or Weekend escape

Elite room stay

Elite room stay
Bridgeport
The price is NZ$603
includes taxes & fees
29 June - 30 June
Elite room stay

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)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is NZ$567
includes taxes & fees
30 June - 1 July
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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 NZ$473
includes taxes & fees
29 June - 30 June
Centric property close to all the great things in the city

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is NZ$580
includes taxes & fees
29 June - 30 June
Stamford Hideaway w/ Fire Pit

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (1 review)
"This hidden gem was a great find!!!! We went to a concert at the Hartford Healthcare Bridgeport Amphitheater and did not want to make the hour plus drive home. We were lucky to find this cute place to stay. It is a basement kitchen, living room ,2 bedroom establishment that is nicely put together and is super clean. We would choose to stay there again if we are in the neighborhood."
United States
Heidi M.
The price is NZ$520
includes taxes & fees
6 July - 7 July
Zen, Spacious & Comfy 2 bed, Lux beds

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is NZ$1,264
includes taxes & fees
14 July - 15 July
3 Mi to Downtown: Spacious White Plains Home

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (4 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is NZ$756
includes taxes & fees
13 July - 14 July
Modern 2 Bed in BlackRock

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 NZ$795
includes taxes & fees
9 July - 10 July
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is NZ$486
includes taxes & fees
3 July - 4 July
Charming 1-bedroom apartment in Carmel with WiFi, AC

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 NZ$556
includes taxes & fees
29 June - 30 June
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

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, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
The price is NZ$565
includes taxes & fees
29 June - 30 June
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 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 NZ$732
includes taxes & fees
29 June - 30 June
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

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 NZ$573
includes taxes & fees
29 June - 30 June
Renovated 2BR Retreat / Modern Comforts Included

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is NZ$486
includes taxes & fees
5 July - 6 July
The Tipsy Gypsy - Studio Apartment

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is NZ$656
includes taxes & fees
20 July - 21 July
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
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

Find out more about New Canaan

Everything you need to know about New Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Canaan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

New Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Canaan holiday rentals we have selected for you start as low as NZ$260 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Canaan rentals

At Expedia, we put the best New Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top New Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 WiFi 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 John Rogers Studio and Museum, whereas Old Stamford Road Bird Sanctuary and God's Acre are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Silvermine Arts 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.