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New Canaan Vacation Rentals

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Browse Select New Canaan Vacation Homes

Our top choices for New Canaan vacation homes

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.8 out of 10, Exceptional, (6)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

4.0 star property
10.0 out of 10, Exceptional, (7)
"This place was perfect for our family members - 7 adults. Everyone had their own bed and there were plenty of pillows and towels for all. It was quite clean and decorated nicely. The kitchen was well stocked with anything we might need and more. Thank you to the excellent hosts!"
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

Business or Weekend escape

9.2 out of 10, Wonderful, (45)
"Very nice owner with great communication. "
The price is CA $118
CA $203 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is CA $242
CA $493 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (44)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (33)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (66)
"Great home to stay. Beautiful area to explore!"
The price is CA $484
CA $915 total
includes taxes & fees
Sep 8 - Sep 9
Captain's Cottage - Cold Spring Harbor Water Views

Spacious 4-bedroom house in charming Rye with AC

The price is CA $277
CA $628 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 4-bedroom house in charming Rye with AC

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is CA $226
CA $435 total
includes taxes & fees
Sep 16 - Sep 17
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (3)
"Check in was super simple and easy. Kitchen area was so clean and neat. Overall stay was a wonderful experience. "
Soothing Carriage House with Hot Tub in charming Stratford

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (26)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

9.8 out of 10, Exceptional, (10)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (3)
"Beautiful home and great host!"
Serene Hudson Valley Escape w/ Pool & Grill

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (13)
"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 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (28)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home

Walk to Putnam Lake: Updated Home w/ Deck

2.0 out of 10, (1)
"Upon opening front door, first floor was visually appealing. Quickly the smell of air freshener and stail wet dog overwhelmed. Upon exploring the bedrooms the "guest room" was lacking all beding and window coverings. Master bedroom as advertised has walk in closets. However these are unusable due to 4 feet of home owners items piled within. Upon futher inspection every closet in the home contained piles of home owners belongings. Provided within the master bathroom were 4 towels, no hand towels...
Walk to Putnam Lake: Updated Home w/ Deck

Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Lovely home for a get away. "
Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.8 out of 10, Exceptional, (12)
"Clean and spacious apartment in a quiet neighborhood."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
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