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In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
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26 Dec - 28 Dec
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23 Jan - 25 Jan

Cottages in New Canaan

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Property grounds

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Cos Cob Cottage- Full Kitchen, Pet Friendly
Exterior

Cos Cob Cottage- Full Kitchen, Pet Friendly

10.0 out of 10, Exceptional, (4)
"2 night stay over Thanksgiving holiday. Cozy Cottage was just lovely. Fully applianced and stocked kitchen. Large bathroom-super soft towels. King size bed was comfy and cozy. Living room was perfect for relaxing. Rules clearly communicated. Owners were very helpful and responsive. Driveway a little tricky to maneuver when parking spots are occupied. Safe location…. Good walking and exploring in the area "
Cos Cob Cottage- Full Kitchen, Pet Friendly
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Terrace/patio

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

8.8 out of 10, Excellent, (9)
"Water view and deck magnificent "
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Westport "Gold Coast" across from Southport beach
Exterior

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (94)
"Easy communication, clean apartment, good location for beach and nearby towns. "
Westport "Gold Coast" across from Southport beach
Second floor cottage apartment located in a private community.
Exterior

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"Great time, nice little private neighborhood! Pretty views if you go for nice walks. 2 great parks near by. Lovely stay. Had everything we needed "
Second floor cottage apartment located in a private community.
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Exterior

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (10)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Fridge, microwave, oven, stovetop

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

10.0 out of 10, Exceptional, (8)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Beach cottage on private beach!
Exterior

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Exterior

Charming Studio-Cottage with WiFi & TV free parking in Greenwich

Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking
Lakefront Brewster Vacation Rental w/ Private Dock
Cottage (3 Bedrooms) | Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (18)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Beach house cottage steps to private beach in the heart of Bayville
Exterior

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (11)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Outdoor dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (33)
"Clean, quaint spot for a family gathering. A little chilly in February but very calming and pleasant stay."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Sun and Fun on the beach!!
Outdoor dining

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (17)
"The house was right on the beach. Awesome view. The entertaining space inside and outside was great. The house was very clean and equipped well. It was laid out very well with perfect sized bedrooms. Our stay was very good."
Sun and Fun on the beach!!
Briarcliff Manor Estate w/ Hudson River Views
House (4 Bedrooms) | Interior

Briarcliff Manor Estate w/ Hudson River Views

3.0 star property
Briarcliff Manor Estate w/ Hudson River Views
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Exterior

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
House (3 Bedrooms) | Interior

Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

3.0 star property
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
Outdoor Entertainment Areas: Spacious Katonah Gem!
House (3 Bedrooms) | Interior

Outdoor Entertainment Areas: Spacious Katonah Gem!

3.0 star property
Outdoor Entertainment Areas: Spacious Katonah Gem!
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

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

10/10 Excellent
"Rooms were nice. "
Peter 2-night trip
Posted 1 day ago
The Armon Stamford Hotel & Conference

Frequently asked questions

How much do cottages in New Canaan cost?
Rates for cottages in New Canaan range between and per night. No matter your budget, you'll find the ideal place to relax and reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in New Canaan?
Stay close to nature in one of the 53 cottages available in New Canaan. To help you select a place that's right for you, take advantage of our filters to search for perks or amenities you need.
Why book your cottage in New Canaan with Expedia?
We think that a vacation should be a walk in the park, so if you're in search of cottages in New Canaan at a competitive rate, Expedia delivers. Keep costs down and opt for a wallet-friendly option far away from the city rush, or book an upscale cottage to really pamper your favorite people.