Holiday Homes in New Canaan

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Check prices for these dates

In two weeks
12 June - 14 June
In two months
24 July - 26 July
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for New Canaan holiday homes

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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$455
includes taxes & fees
1 June - 2 June
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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
7.0 out of 10, Good, (14 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is AU$371
includes taxes & fees
5 June - 6 June
Centric property close to all the great things in the city
Outdoor dining

Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout
Cove - East Side - Shippan
Stamford : The Comfy Cove Hideout
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$207
includes taxes & fees
15 June - 16 June
Business or Weekend escape
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
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$489
includes taxes & fees
1 June - 2 June
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Marina

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (78 reviews)
"Location was perfect!"
United States
Linda J P.
Captain's Cottage - Cold Spring Harbor Water Views
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)
"Very clean, modern and comfortable. Host was helpful and a great communicator. We will definitely stay again! "
United States
Tricia H.
The price is AU$545
includes taxes & fees
29 May - 30 May
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Dining

Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is AU$955
includes taxes & fees
31 May - 1 June
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is AU$575
includes taxes & fees
17 June - 18 June
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Beach nearby, sun-loungers, beach towels

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (34 reviews)
"Hosts were readily available to address any needs that arose. Home was comfortable for our weekend visit."
United States
Meg S.
The price is AU$774
includes taxes & fees
31 May - 1 June
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fridge, microwave, oven, stovetop

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AU$806
includes taxes & fees
31 May - 1 June
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AU$1,272
includes taxes & fees
2 June - 3 June
Stylish Beach Home near Stamford Downtown/Beach
Fridge, microwave, stovetop, dishwasher

NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very good, (15 reviews)
"Host was very communicative. "
United States
Joe W.
The price is AU$1,229
includes taxes & fees
31 May - 1 June
NYC-Area Escape Near River, Trails & MTA!
Beach nearby, sun-loungers, beach towels

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac
10.0 out of 10, Exceptional, (16 reviews)
"Very clean and cozy home "
United States
Brian D.
The price is AU$1,234
includes taxes & fees
23 June - 24 June
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Interior

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is AU$1,125
includes taxes & fees
8 June - 9 June
Walkable Townhouse with Garage & Yard, 45 min to NYC!
Smart TV, fireplace, books, stereo

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (11 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is AU$868
includes taxes & fees
31 May - 1 June
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
TV

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking
Cove - East Side - Shippan
8.0 out of 10, Very good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is AU$615
includes taxes & fees
29 May - 30 May
Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking
Fridge, microwave, oven, stovetop

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 Beach
10.0 out of 10, Exceptional, (24 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is AU$1,262
includes taxes & fees
17 June - 18 June
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Fridge, microwave, oven, stovetop

Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
8.4 out of 10, Very good, (6 reviews)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is AU$1,076
includes taxes & fees
31 May - 1 June
Modern + Spacious 5BR/2BA Home, Renovated Backyard
Fridge, microwave, oven, stovetop

Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AU$1,102
includes taxes & fees
1 June - 2 June
Renovated Retreat with Heated Pool
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"The layout of the hotel is a tad complicated but overall the service and amenities including breakfast was really good. I appreciated the extra time for check out."
Johana 1-night trip
Posted 1 hour ago
Hampton Inn White Plains/Tarrytown

Find out more about New Canaan

New Canaan Holiday Homes information

Number of reviews
343
Accommodation
333 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$1,272