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Search Holiday Rentals in New Canaan

Top Holiday Rentals in New Canaan

Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is €301
includes taxes & fees
2 Jun - 3 Jun
DUNE Fairfield Beach
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, (3)
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
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Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (12)
"Super clean, comfortable, and great for overnight stay. Will definitely be back!"
Westport Paradise With Every Amenity!
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (14)
"We loved our stay at the bungalow last weekend. Donna equipped the home with everything needed for a comfortable stay, and more. It is located in a quiet area steps from the Milford Point Audubon center, Wheeler Marsh and Cedar beach. We walked to the Walnut Beach area where there are a few shops and restaurants, most notably a delicious Mexican restaurant and coffee shop. A perfect get away, despite the questionable weather."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
10.0 out of 10, Exceptional, (1)
"The location within walking distance church"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
1 bedroom, WiFi, bed sheets
Charming Private Oasis in Old Greenwich – A Commuter's Dream!
10.0 out of 10, Exceptional, (1)
"the owners were on property and very accommodating, the unit was pristine with lots of little extras. would definitely stay there again. "
Charming Private Oasis in Old Greenwich – A Commuter's Dream!
Balcony
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
10.0 out of 10, Exceptional, (9)
"Our family gathered for a dinner with 22 people on the patio and the setting and house made that possible and it was lovely. 30 family members came to practice a dance on the back lawn and we had space in the house for them to relax and visit. Our family of 10 was very comfortable and found the accommodations tasteful and renovations were lovely! I would give a 5+ rating and thanks to Alex, who was so helpful before we arrived, with questions about the house."
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Fridge, microwave, oven, stovetop
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Beach nearby, sun-loungers, beach towels
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Fridge, microwave, stovetop, coffee/tea maker
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, (3)
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is €255
includes taxes & fees
31 May - 1 Jun
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Pool
Business or Weekend escape
9.8 out of 10, Exceptional, (11)
"Everything was great at the property. And the apartment was spotless and it had refreshments. We really loved the place. We probably will be back soon. The owner was very nice and great to work with. Thank you for your hospitality"
The price is €133
includes taxes & fees
20 May - 21 May
Business or Weekend escape
Marina
OCEAN COAST LUXURY BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC
9.8 out of 10, Exceptional, (17)
"Great place, easy process. Exactly as advertised. Owner took the time to leave tips about where to go when arriving. Top notch all around."
OCEAN COAST LUXURY BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH, 45 MIN TO NYC
Fridge, microwave, dishwasher, coffee/tea maker
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (13)
"This was walking distance to the Total Mortgage Arena for our robotics competition. Having the full kitchen to cook meals was awesome. Nice comfy beds, plenty of space, I claimed the nook off the kitchen/dining area for myself. Boys had front room to work on their robot."
Cheerful 4 bedrooms residential house.
Cozy house on the Hudson
9.6 out of 10, Exceptional, (33)
"A beautiful home in a neighborhood that is right on the Hudson. Host was informative and helpful. Would definitely stay again and recommend to all!"
Cozy house on the Hudson
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (20)
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Terrace/patio
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (8)
"Paul was very communicative and helpful. We did not like the neighborhood but once you enter the apartment it’s a whole different story. The apartment was very clean and spacious. As mentioned in another review, it needs coverings on all windows for privacy from the neighbors."
The price is €384
includes taxes & fees
21 May - 22 May
Luxury Designer 2 bedroom+office/3bed vacation home.
Studio Suite, Kitchen | Private kitchen | Mini-fridge, coffee/tea maker
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, (37)
"The pictures are very deceiving - as they are of the Guesthouses not the main hotel. I thought I was booking at an Inn, but I was really booked at a regular ole chain hotel. One that charges $8 per person per day for their pool! (you should really change this policy for paying overnight guests - why should we pay additional for facilities like this?) There's also nowhere to walk to from here, so if you're without a car expect to be paying for Ubers everywhere (which is fine as they're readily...
Guesthouse at Norwalk Inn
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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.

Other types of properties in New Canaan you may be interested in

Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, (1501)
"Pretty decent although an older property. Help very friendly. Breakfast included but they need better bagels."
The price is €106
includes taxes & fees
19 May - 20 May
Amsterdam Hotel
Individually decorated, individually furnished, desk, laptop workspace
EVEN Hotel Norwalk, an IHG Hotel
3.5 star property
8.4 out of 10, Very good, (1005)
"Excellent customer service "
The price is €132
includes taxes & fees
10 Jun - 11 Jun
EVEN Hotel Norwalk, an IHG Hotel
Desk, laptop workspace, blackout curtains, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1004)
"Always clean. Good breakfast, rates are good"
The price is €126
includes taxes & fees
27 May - 28 May
Baymont by Wyndham White Plains - Elmsford
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.

Frequently asked questions

Can I find a holiday rental in New Canaan?

Yes, there are holiday rentals in New Canaan close to Goldenberry, or you can select a more secluded option if you're looking for a relaxing stay. New Canaan is known for its seafood restaurants.

How many holiday rentals will I find in New Canaan?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your New Canaan stay.

What can I see and do in New Canaan?

Cultural attractions include The Glass House and Silvermine Arts Center, whereas Waveny Park and God's Acre are a couple of picturesque spots to enjoy the outdoors. Glass House Visitor's Center and New Canaan Town Hall are other places to visit while you're in town.

What are holiday rentals like in New Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Canaan. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.

Recent reviews of New Canaan properties
Expedia verified reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

5/5 Excellent
"We had a pleasant stay on our way north. The hotel is super convenient off I 95 but it doesn't feel like a highway hotel. Very affordable price, like that it's dog friendly."
A verified traveller stayed at The Circle Hotel Fairfield
Posted 1 day ago
The Circle Hotel Fairfield