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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in New Canaan

Dining tables
The ARLO - Walk to Brewery and Restaurants

The ARLO - Walk to Brewery and Restaurants

Milford
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is SAR 507
SAR 1,369 total
includes taxes & fees
9 Dec - 10 Dec
The ARLO - Walk to Brewery and Restaurants
Pool
Business or Weekend escape

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is SAR 319
SAR 550 total
includes taxes & fees
1 Jan - 2 January 2026
Business or Weekend escape
Dining
Soothing 4-bedroom house with AC in Trumbull

Soothing 4-bedroom house with AC in Trumbull

Trumbull
The price is SAR 3,377
SAR 4,346 total
includes taxes & fees
4 Jan - 5 January 2026
Soothing 4-bedroom house with AC in Trumbull
Fridge, microwave, oven, stovetop
The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office

Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8)
"Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay."
United States
George M.
The price is SAR 1,074
SAR 2,523 total
includes taxes & fees
8 Dec - 9 Dec
The B&W Haven 5BR Home with yard theater + Office
Fridge, microwave, oven, stovetop
Upscale 4BR Retreat at the Reservoir!

Upscale 4BR Retreat at the Reservoir!

Reservoir
The price is SAR 2,158
SAR 3,472 total
includes taxes & fees
15 Dec - 16 Dec
Upscale 4BR Retreat at the Reservoir!
Fridge, oven, stovetop, coffee/tea maker
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, (13)
"This rental was great accommodation"
United States
Alma B.
The price is SAR 591
SAR 1,116 total
includes taxes & fees
5 Dec - 6 Dec
Centric property close to all the great things in the city
5 bedrooms, desk, iron/ironing board, free WiFi
Modern + Spacious 5BR/2BA Home, Renovated Backyard

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

West End - West Side
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is SAR 1,334
SAR 2,902 total
includes taxes & fees
7 Dec - 8 Dec
Modern + Spacious 5BR/2BA Home, Renovated Backyard
Front of property
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is SAR 2,702
SAR 4,421 total
includes taxes & fees
8 Dec - 9 Dec
Beechmont - Perfect for Family Retreat!
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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

North End
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
The price is SAR 2,702
SAR 5,188 total
includes taxes & fees
5 Dec - 6 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Interior
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

Fairfield
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
The price is SAR 3,002
SAR 7,580 total
includes taxes & fees
7 Dec - 8 Dec
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
Fridge, microwave, oven, stovetop
Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit

North End
9.8 out of 10, Exceptional, (7)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is SAR 680
SAR 1,671 total
includes taxes & fees
9 Dec - 10 Dec
Marine Theme - 4 BR - Backyard - Fire pit
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is SAR 450
SAR 739 total
includes taxes & fees
14 Dec - 15 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Property grounds
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Fairfield
9.4 out of 10, Exceptional, (20)
"Very nice house and location. Very good service and excellent attention."
Mexico
Armando V.
The price is SAR 1,216
SAR 2,786 total
includes taxes & fees
7 Dec - 8 Dec
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Outdoor dining
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Fairfield
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is SAR 770
SAR 1,894 total
includes taxes & fees
8 Dec - 9 Dec
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fridge, microwave, oven, stovetop
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Fairfield
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is SAR 687
SAR 1,825 total
includes taxes & fees
7 Dec - 8 Dec
Bright Escape, Top-Rated Design, Fire pit, Near Beach
Outdoor dining
Nature Meets Village - Walkable Northport

Nature Meets Village - Walkable Northport

Northport
The price is SAR 1,952
SAR 2,839 total
includes taxes & fees
18 Dec - 19 Dec
Nature Meets Village - Walkable Northport
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)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
United States
Patrick
The price is SAR 769
SAR 1,496 total
includes taxes & fees
3 Jan - 4 January 2026
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Exterior
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
Norwalk
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
The price is SAR 1,062
SAR 2,285 total
includes taxes & fees
21 Dec - 22 Dec
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Smart TV, fireplace, table tennis, computer monitors
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, (73)
"Location was perfect!"
United States
Linda J P.
The price is SAR 773
SAR 1,784 total
includes taxes & fees
8 Dec - 9 Dec
Captain's Cottage - Cold Spring Harbor Water Views
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Peaceful Vintage Home with Private Pond in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is SAR 1,858
SAR 2,854 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful Vintage Home with Private Pond in Redding, CT.
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"This was the best dog friendly hotel I’ve ever stayed in. Clean room, excellent kitchenette and bathroom amenities, and free breakfast. The room heater was a bit loud when it turned on, which was the only negative aspect of our experience. Great stay! "
Nancy 1-night trip
Posted 1 day ago
The Circle Hotel Fairfield