Vacation Homes in New Canaan, CT

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Top Vacation Homes in New Canaan

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 CT
$238 nightly
The price is $269 total per night
$269 total
Dec 21 - Dec 22
Total with taxes and fees
A garden is available at this vacation home.
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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

Bridgeport CT
$1,403 nightly
The price is $1,587 total per night
$1,587 total
Dec 21 - Dec 22
Total with taxes and fees
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
Peaceful Vintage Home with Private Pond in Redding, CT.

Peaceful Vintage Home with Private Pond in Redding, CT.

2 out of 5
Redding CT
$618 nightly
The price is $701 total per night
$701 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Charming Home in Seaside

Charming Home in Seaside

2 out of 5
Bridgeport CT
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This vacation home features laundry facilities.
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY
$420 nightly
The price is $480 total per night
$480 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Stareway to Heaven Su

Stareway to Heaven Su

Fairfield CT
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This vacation home includes a garden and laundry facilities.
Westport Gem - walk to shops, dining, town center, pet-friendly

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport CT
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This vacation home features laundry facilities.
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Fairfield CT
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This vacation home features laundry facilities.
Spacious 4-bedroom house in charming Rye with AC

Spacious 4-bedroom house in charming Rye with AC

Rye NY
$2,502 nightly
The price is $2,502 total per night
$2,502 total
Dec 21 - Dec 22
Total with taxes and fees
Stay at this vacation home in Rye. Enjoy air conditioning. Popular attractions Rye Playland and Emelin Theatre are located nearby.
Business or Weekend escape

Business or Weekend escape

Stratford CT
$130 nightly
The price is $147 total per night
$147 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This vacation home includes a garden and barbecue grills.
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 NY
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A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the playground, barbecue grills, and childcare. A garden and laundry facilities are also provided.
Ultra-Modern Luxe Sleek & Stunning Stay

Ultra-Modern Luxe Sleek & Stunning Stay

2 out of 5
White Plains NY
$675 nightly
The price is $772 total per night
$772 total
Dec 23 - Dec 24
Total with taxes and fees
This vacation home features laundry facilities.
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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.

Top hotels in New Canaan

Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
$183 nightly
The price is $209 total per night from Dec 28 to Dec 29
$209 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (1,156 reviews)

Find the Best Vacation Homes in New Canaan

Why book a vacation home in New Canaan?

Vacation homes in New Canaan make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in New Canaan?

Private New Canaan rental homes range between $124 - $2,502 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in New Canaan vacation home rentals. You might look for New Canaan rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in New Canaan offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in New Canaan?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in New Canaan. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding New Canaan hotels and vacation homes that best suit your stay. We also have deals for flights, and New Canaan car rentals. You’ll save even more when you bundle your items into a New Canaan vacation package!

How many vacation homes are available to book in New Canaan?

There are 335 rental homes in New Canaan. Enter your travel dates to check availability.

How do I find the best price for a vacation home in New Canaan?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

New Canaan Vacation Homes essential information

Accommodation
335 Vacation Homes
Lowest Price
$124
Highest Price
$2,502
Popular accommodation
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock., Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!, Peaceful Vintage Home with Private Pond in Redding, CT., Charming Home in Seaside, Captain's Cottage - Cold Spring Harbor Water Views, Stareway to Heaven Su, Westport Gem - walk to shops, dining, town center, pet-friendly, Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train , Spacious 4-bedroom house in charming Rye with AC, Business or Weekend escape, Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC, Ultra-Modern Luxe Sleek & Stunning Stay

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