A highway surrounded by autumn foliage.

Search New Canaan Cottage Rentals from CA $605

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for New Canaan cottages

A wooden deck with a railing overlooking a well-maintained lawn and trees.

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.6 out of 10, Exceptional, (10 reviews)
"lovely porch and backyard."
United States
Kaia W.
The price is CA $567
CA $1,560 total
includes taxes & fees
Nov 4 - Nov 5
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A two-story house with a white picket fence, a garage, and a tree in front.

2. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (18 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is CA $415
CA $778 total
includes taxes & fees
Oct 18 - Oct 19
Nama-stay, sweet pink Saugatuck Shores beach cottage
A two-story house with a white picket fence, a front porch, and a visible staircase leading to the entrance.

3. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is CA $866
CA $1,316 total
includes taxes & fees
Oct 16 - Oct 17
4 Mi to Beach & Dtwn! Charming Fairfield Home
A wooden deck with a railing overlooking a body of water and trees.

4. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (25 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is CA $355
CA $605 total
includes taxes & fees
Oct 15 - Oct 16
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden house with a stone pathway leading to a wooden deck.

5. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is CA $1,145
CA $2,249 total
includes taxes & fees
Oct 19 - Oct 20
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A two-story house with a front yard, a staircase, and a covered outdoor seating area.

6. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is CA $388
CA $1,159 total
includes taxes & fees
Oct 21 - Oct 22
Snow Days & City Escapes: Spacious Ossining 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Canaan Hotel Reviews

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

8/10 Good
"The front desk"
Robert 1-night trip
Posted 2 hours ago
The Armon Stamford Hotel & Conference

Find out more about New Canaan

New Canaan Cottages information

Number of reviews
53
Accommodation
60 Cottages
Lowest Price
CA $605
Highest Price
CA $2,249

Frequently asked questions

How much do cottages in New Canaan cost?
Rates for cottages in New Canaan range between CA $605 and CA $2,249 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 60 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.
How can I find cheap cottages in New Canaan?
Expedia is here to help you easily locate cheap cottages in New Canaan. To find your ideal stay in a matter of clicks, try out our convenient filter tool to refine your search results by amenities, star rating and budget.
What is there to do in New Canaan near my cottage?
If you're eager to fill up your itinerary in New Canaan, pay a visit to Waveny Park. It's a hit with travelers and locals alike.

Explore a world of travel with Expedia