Photo by (yu+ma)

Search Vacation Homes in New Canaan

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 367 Vacation Homes in New Canaan with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (7)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (58)
"Everything was awesome! Would definitely stay here again! "
The price is AED 1,359
AED 2,543 total
includes taxes & fees
15 May - 16 May
Captain's Cottage - Cold Spring Harbor Water Views

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (20)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (105)
"My friends and I were in town for a wedding."
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
27 Apr - 28 Apr
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"We stayed for 3 weeks it was lovely!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (31)
"The house was in a great location, was well-stocked and clean, and the host was very responsive. Would definitely stay here again and highly recommend. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is AED 1,723
AED 3,382 total
includes taxes & fees
28 Apr - 29 Apr
New Beach Home near Stamford Downtown/Shippan

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"Great place magnificent views. It’s a very peaceful place"
Cottage at Sunny Day- Lakeside, views, kayak, dock

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (14)
"We enjoyed staying here for a long weekend while touring maritime colleges in the area. This nice quiet neighborhood was restful at the end of each day and convenient to everywhere we needed to be. The nearby brewery on the harbor was a great spot for lunch."
Glen Cove Home: Walk to Boardwalk + Dining!

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

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Ossining Vacation Rental Near River, Trails & MTA!

8.4 out of 10, Very Good, (7)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house
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.
Don't see what you're looking for?
See all available properties in New Canaan
Save an average of 15% on thousands of hotels when you're signed in

Other property types in New Canaan

Stamford Suites

3.0 star property
5.8 out of 10, (28)
"Convenience. Full kitchen and spacious rooms"
The price is AED 691
AED 794 total
includes taxes & fees
30 Apr - 1 May
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is AED 1,606
AED 2,049 total
includes taxes & fees
2 May - 3 May
DUNE Fairfield Beach

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains
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.