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Holiday Homes in New Canaan

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Featured Holiday Homes in New Canaan

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$220
includes taxes & fees
26 Nov - 27 Nov
Business or Weekend escape

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lakeview Estate - Chef's Kitchen - NYC Getaway

10.0 out of 10, Exceptional, (23)
"Fantastic place! Beautiful views, lots of room, comfy beds, clean. There was 10 of us and it was a delight. Highly recommend it. "
Lakeview Estate - Chef's Kitchen - NYC Getaway

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (19)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
The price is AU$1,632
includes taxes & fees
30 Nov - 1 Dec
Stylish Beach Home near Stamford Downtown/Beach

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (10)
"We had a good time staying at this and the adjoining property. "
Glen Cove Home: Walk to Boardwalk + Dining!

Amazing 3BR/3BA! Croton on Hudson!

7.0 out of 10, Good, (2)
"We found the house pleasant and centrally located"
Amazing 3BR/3BA! Croton on Hudson!

The ARLO - Walk to Brewery and Restaurants

10.0 out of 10, Exceptional, (1)
"Great proximity to restaurants graduation venue, Sacred Heart. We had a great time. The property is clean private, and really really cute."
The ARLO - Walk to Brewery and Restaurants

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 AU$883
includes taxes & fees
9 Dec - 10 Dec
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, (2)
"This apartment was perfect for our long weekend! Very quiet place and neighborhood, with easy walk to the train and deli. Hosts were very good with communication!"
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is AU$655
includes taxes & fees
9 Dec - 10 Dec
Captain's Cottage - Cold Spring Harbor Water Views

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

9.8 out of 10, Exceptional, (60)
"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

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.

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (105)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!

10.0 out of 10, Exceptional, (23)
"Wonderful house. Comfortable beds. Amazing lake view. Great location. We stayed for 3 nights and enjoyed it so much."
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!

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 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!

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (14)
"Beautiful property— even more than the pictures (which is often rare). Quiet, scenic, and spacious. Communication with the host was very good and helpful."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (23)
"The property is absolutely stunning, very peaceful and Zen! Olga is fantastic very caring and attentive to detail. This was the perfect anniversary getaway and I can’t wait to go back."
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
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, (766)
"All is well"
The price is AU$254
includes taxes & fees
30 Nov - 1 Dec
Stamford Suites

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$220
includes taxes & fees
26 Nov - 27 Nov
Business or Weekend escape

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"Beautiful and convenient location in a pretty neighborhood. Fairlt quiet on the 3rd floor, although some late night noise from party-ers but that was made clear on the website. Walkable to town and beach. Very comfortable stay! Thank you!"
The price is AU$431
includes taxes & fees
25 Nov - 26 Nov
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.
Beautiful view of the beach with palm trees

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