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Compare 292 Vacation Homes in New Canaan with updated reviews, rates, and availability.

Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is SAR 281
SAR 507 total
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
The price is SAR 1,840
SAR 3,703 total
includes taxes & fees
25 Sep - 26 Sep
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (39)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Ossining Vacation Rental Near River, Trails & MTA!
Ossining Vacation Rental | 5BR | 3.5BA | 2,800 Sq Ft | Stairs Required
Ossining Vacation Rental Near River, Trails & MTA!
6.0 out of 10, (2)
"The house was nice & spacious. I do feel like it could use more seating in the living room, considering it can hold up to 11 guests. It would aslo be nice if there were tv's in the guest rooms upstairs. Also, maybe make sure the cleaning crew removes cobweks. "
Ossining Vacation Rental Near River, Trails & MTA!
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
SUNSET OF MARSH & OCEAN
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (21)
"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
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (22)
"We had an absolutely fantastic stay at this lakefront property! The outdoor gathering spots are plentiful and perfect for family and friends to enjoy the beautiful surroundings. Whether it was morning coffee on one of the many decks, or simply lounging in the sun, every moment was magical. The kitchen was incredibly well-stocked with everything we needed to prepare meals, which made our stay even more convenient and enjoyable. The entire place was spotless, and it was clear that a lot of care...
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
View of the front and outside of house with driveway and garage.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (87)
"Excellent! Loved it! Home was more spacious than we ever thought. The rooms had so much character! Beautiful yard. Perfect setting. We would stay here again."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Living area
Quaint duplex with private yard. Walk to beach, dining, & shopping!
10.0 out of 10, Exceptional, (35)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Lakeside luxury: beautiful, relaxing 4 bedroom home
Sit back and relax!
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Historic Connecticut Home w/ Grill & Spacious Yard
Weston Vacation Rental | 3BR | 2.5BA | 2,800 Sq Ft | Stairs Required
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (2)
"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
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Interior
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (15)
"We stayed at this unit for one week while our son participated at a camp at Sacred Heart University. This unit is located close to Fiarfield beaches - we brought our bikes and started each day with a ride to the ocean and dip in the water. It is also walking distance to restaurants and shops. The unit has everything you need to cook and is absolutely spotless! A big bonus was bringing our furry child (golden retriever). The manager is responsive and helpful. Highly recommend this unit!"
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Cheerful 4 bedrooms residential house.
Exterior
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (20)
"My friends and I stayed in Bridgeport for a weekend of music, and we had a great experience here! The owners were responsive and the place was exactly what we needed"
Cheerful 4 bedrooms residential house.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Adorable Cottage with Water Views, Across the street from Prime & other eateries
10.0 out of 10, Exceptional, (58)
"Great location, attentive host. Very cute cottage - with everythng we beed. Cute outside (covered) space to relax. "
Adorable Cottage with Water Views, Across the street from Prime & other eateries
2 mini-bedrooms apartment with antique bathtub.
Private kitchen
2 mini-bedrooms apartment with antique bathtub.
10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Charming duplex with private yard. Close to the beach, dining & shopping!
Living area
Charming duplex with private yard. Close to the beach, dining & shopping!
9.8 out of 10, Exceptional, (34)
"Wonderful property that is very clean and in a peaceful area. 3 good size rooms and a clean bathroom. No concerns for the entire stay. Recommend that you check out the giant Gorilla statue at the Bruce Museum for sure! For others who may be concerned (accessibility) If you have trouble with walking or stairs the area can be a challenge. There is a narrow staircase (which can be good for some) and a lot of stairs to get to the front door. The house is also located on a steep hill. So if you...
Charming duplex with private yard. Close to the beach, dining & shopping!
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Mamaroneck Vacation Rental | 3BR | 3BA | 1 Step Required | 1,997 Sq Ft
Charming Mamaroneck Home ~ 22 Mi to Manhattan
7.8 out of 10, Good, (8)
"The property is as advertised. It was extremely convenient, located two minutes from I-95. You can go north on I-95 to I-287 to head towards Rockland County, as well as to connect to I-684. You can also take Mamaroneck Ave north to the Hutchinson River Parkway or south into town to explore and find some nice restaurants. We used the house as a base of operations. It is clean user friendly."
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Catch some Zzz at Black Rock Harbor
Enjoy banquet dining adjacent to the kitchen, while savoring the gentle breezes and soothing sounds emanating from the nearby Seabright Beach.
Catch some Zzz at Black Rock Harbor
10.0 out of 10, Exceptional, (11)
"Loved this modernized beach cottage. Walking distance to food and Bev as well as the beach. Quiet neighborhood. Perfect stay. "
Catch some Zzz at Black Rock Harbor
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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.
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Other property types in New Canaan

Stamford Suites
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (747)
"It was more than i expected. "
The price is SAR 571
SAR 640 total
includes taxes & fees
7 Oct - 8 Oct
Stamford Suites
DUNE Fairfield Beach
Room
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (35)
"Enjoyed the stay in the modern suite, located a short walk to the beach. Recommend the hotel and touring in the Fairfield, CT area. "
DUNE Fairfield Beach
Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is SAR 281
SAR 507 total
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
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.