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Compare 288 Vacation Homes in New Canaan with updated reviews, rates, and availability.

Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is AED 275
AED 496 total
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
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
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
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (47)
"Wonderful stay. The home and town were a great location for our family trip!"
The price is AED 1,054
AED 2,011 total
includes taxes & fees
1 Oct - 2 Oct
Captain's Cottage - Cold Spring Harbor Water Views
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"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!
Family-Friendly, Near-NYC Norwalk Retreat
2.0 star property
10.0 out of 10, Exceptional, (2)
"Met all of our expectations, made a very enjoyable stay with 2 little ones. Host was accommodating and went above and beyond to support our needs. "
The price is AED 686
AED 1,939 total
includes taxes & fees
8 Oct - 9 Oct
Family-Friendly, Near-NYC Norwalk Retreat
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
2.0 star property
8.0 out of 10, Very Good, (1)
"The apartment was clean, neat and most things looked new. AC was in windows. Dead end street and very quiet."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
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
10.0 out of 10, Exceptional, (59)
"We enjoyed our short stay at the cottage! The thoughtful amenities were appreciated (especially ALL your coffee needs except dairy, toiletries, filtered water ready in the fridge), and there were probably more we didn’t take advantage of…we were only there for 3 days and didn’t cook in the house but noticed the pantry was stocked with spices and cooking essentials. The beds and bedding were very comfortable. The outdoor area was lovely and well maintained but we didn’t use it much because of...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
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.
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
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!
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
10.0 out of 10, Exceptional, (7)
"Excellent place with alot to do in the surrounding area. Would 100% recommend to anyone"
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
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
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
Centric property close to all the great things in the city
8.2 out of 10, Very Good, (10)
"This rental was great accommodation"
The price is AED 569
AED 1,089 total
includes taxes & fees
14 Oct - 15 Oct
Centric property close to all the great things in the city
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
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
Charming Mamaroneck Home ~ 22 Mi to Manhattan
7.8 out of 10, Good, (9)
"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
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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
2.5 star property
6.8 out of 10, (748)
"It was more than i expected. "
The price is AED 559
AED 626 total
includes taxes & fees
11 Oct - 12 Oct
Stamford Suites
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is AED 275
AED 496 total
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (36)
"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
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.