A highway surrounded by autumn foliage.

New Canaan Vacation Rentals

  • 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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for New Canaan vacation rentals

A modern hotel room with a large bed, a wooden floor, a small kitchenette, and a view of the city through large windows.

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful setting, and plenty of room for a family of four. Accommodations were very clean and spacious. Thank you for hosting us!"
United States
Susan K.
The price is ￥49,468
￥107,994 total
includes taxes & fees
Nov 29 - Nov 30
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ￥50,720
￥58,328 total
includes taxes & fees
Dec 1 - Dec 2
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,943
￥41,741 total
includes taxes & fees
Nov 22 - Nov 23
DUNE Fairfield Beach
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

4. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥20,631
￥38,215 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Studio with Pool Table
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

5. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is ￥22,116
￥25,433 total
includes taxes & fees
Nov 8 - Nov 9
Stamford Suites
Living area

6. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is ￥23,624
￥40,554 total
includes taxes & fees
Nov 11 - Nov 12
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern living room with a sofa, a coffee table, and a bar stool.

7. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥22,679
￥46,082 total
includes taxes & fees
Nov 20 - Nov 21
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern kitchen with a central island, pendant lights, and built-in shelves.

8. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is ￥33,756
￥47,100 total
includes taxes & fees
Nov 30 - Dec 1
Stylish Home With Free ParkingZA
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

9. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥22,679
￥62,618 total
includes taxes & fees
Nov 8 - Nov 9
Modern Luxe 1BR Apt in Downtown Stamford
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥27,639
￥53,204 total
includes taxes & fees
Nov 8 - Nov 9
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern living room with a grey sofa, a small round coffee table, and a dining area with a kitchen in the background.

11. Romantic hideout. 1Br. Lower Level

Romantic hideout. 1Br. Lower Level
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is ￥22,639
￥45,847 total
includes taxes & fees
Nov 23 - Nov 24
Romantic hideout. 1Br. Lower Level
An outdoor seating area with a round table, a chair, and a hanging light fixture.

12. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is ￥35,317
￥70,018 total
includes taxes & fees
Nov 9 - Nov 10
Gem by the water+ firepit and all fenced backyard
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
The price is ￥47,544
￥84,985 total
includes taxes & fees
Nov 11 - Nov 12
Nama-stay, sweet pink Saugatuck Shores beach cottage
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

14. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥54,334
￥86,934 total
includes taxes & fees
Nov 9 - Nov 10
Gilded Age Luxury Surrounded by Nature
A modern kitchen with white cabinets, a marble island, and black bar stools.

15. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is ￥48,475
￥107,096 total
includes taxes & fees
Nov 10 - Nov 11
Spacious Retreat with Game Room and Fire Pit
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

16. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is ￥47,090
￥58,091 total
includes taxes & fees
Nov 9 - Nov 10
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A living room with a sofa, armchair, ottoman, and coffee table.

17. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥31,868
￥70,036 total
includes taxes & fees
Nov 11 - Nov 12
Stamford Home | Family, Work and Plenty of Parking
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

18. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is ￥38,837
￥95,540 total
includes taxes & fees
Nov 9 - Nov 10
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

19. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
8.0 out of 10, Very good, (2 reviews)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥31,341
￥53,996 total
includes taxes & fees
Nov 9 - Nov 10
Modern Luxury 1BR Stamford Getaway
A modern kitchen with a central island, pendant lights, and built-in shelves.

20. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is ￥33,545
￥46,806 total
includes taxes & fees
Nov 19 - Nov 20
Stylish Home and Cozy200
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"This hotel is great value for the service the staff provides. It is an older hotel but the room was very clean and the public areas were very good. I liked the plate of small bites like grapes and small pastries when one arrives. The hotel was very convenient to both Westport and Norwalk. We were having dinner and seeing a play at the Westport Playhouse and the Inn was only a few miles away from our destination."
Tanya 1-night trip
Posted 1 hour ago
Norwalk Inn & Conference Center

Find out more about New Canaan

Search for holiday rentals in New Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in New Canaan using one of the methods below:

  • View our selection of featured holiday rentals in New Canaan
  • Use the map to find apartments and other holiday homes in the New Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Canaan while they last

Look no further and take a look at our great range of rental properties in New Canaan!

Frequently asked questions

Can I find a vacation rental in New Canaan?

Yes, you can find vacation rentals in New Canaan near Silvermine Arts Center, or you can go with a secluded option if you want a relaxing stay. New Canaan is known for its seafood restaurants.

What are some of the best vacation rentals that New Canaan has to offer?

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!: Visitors like this New Canaan vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in New Canaan?

With 4 Expedia vacation rentals, you're sure 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 John Rogers Studio and Museum, whereas God's Acre and Old Stamford Road Bird Sanctuary are a couple of picturesque spots to enjoy the outdoors. New Canaan Library and Silvermine Arts Center are other places to visit while you're in town.

What are vacation rentals like in New Canaan?

Vacation rentals are private accommodations you can book for a couple days or more in New Canaan. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.