Holiday rentals in New Canaan

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Top-rated holiday rentals in New Canaan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Flat in Norwalk
4.91 out of 5 average rating, 361 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Top guest favourite
A dining area features a round wooden table set for four, surrounded by upholstered chairs. Natural light floods the space through large windows with simple drapes. A comfortable sofa and TV are positioned in the adjacent living area, complemented by modern lighting fixtures.
Flat in Stamford
4.95 out of 5 average rating, 130 reviews

Luxurious 1BR Downtown Stamford

Step into your luxurious haven in the heart of downtown Stamford, where opulence seamlessly meets comfort and indulgence becomes your personal mantra. From the impeccable design and luxurious amenities to the prime location, every moment spent here is a celebration of the finer things in life. Treat yourself to an extraordinary stay, crafting memories that will linger in your heart for a lifetime . Welcome to a world where luxury knows no bounds, and warm hospitality eagerly awaits your arrival

Top guest favourite
A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.
Guest suite in Wilton
4.92 out of 5 average rating, 166 reviews

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Top guest favourite
Home in Wilton
4.97 out of 5 average rating, 145 reviews

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Top guest favourite
Flat in South Norwalk
4.99 out of 5 average rating, 112 reviews

S. Norwalk Apt near the water!

Newly-built sunny studio apartment with separate eat-in kithchen and spacious bath, across the street from the water in the peaceful waterfront community of Shorefront Park in South Norwalk. 15 min. walk to South Norwalk shops, restaraunts and the train station (65 min train ride to NYC). Private kepypad entrance, washer/dryer, eat-in kitchen, free off-street parking, wifi, central AC. Please note the house next door may be under construction. Please inquire for current status.

Guest favourite
The exterior of a red-brick building is featured, showcasing large black doors with decorative accents. Planters with greenery are placed on either side of the entrance. An iron fire escape extends above the doorway, while a flag hangs on the right side of the image.
Flat in Wall Street
4.97 out of 5 average rating, 155 reviews

"Triplex Historic Beauty" with Seasonal Garden

Featured on the History Channel hit TV series "American Pickers"! Come join us at the head of the harbor in historic downtown Norwalk "Wall Street" neighborhood. This cozy second floor rental has been tastefully decorated with new and old. In addition to the photo descriptions we have included a floor plan for review. Please note the neighborhood is a working waterfront during the day and the Danbury active train line runs behind the building which adds to the character .

Guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 114 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest favourite
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.8 out of 5 average rating, 261 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favourite
Cottage in South Salem
4.96 out of 5 average rating, 260 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Guest favourite
A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guest house in Westville
4.92 out of 5 average rating, 338 reviews

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

Top guest favourite
Home in West Side
4.99 out of 5 average rating, 192 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Top guest favourite
A modern white structure with large windows is surrounded by lush greenery, including a prominent tree and shrubs. A small seating area with a table and chairs is visible in the gravel courtyard, providing a tranquil outdoor setting embraced by nature.
Guest house in Southport
4.97 out of 5 average rating, 214 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

Popular amenities for New Canaan holiday rentals

When is the best time to visit New Canaan?

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Avg. price$253 SGD$228 SGD$266 SGD$249 SGD$228 SGD$257 SGD$285 SGD$228 SGD$223 SGD$286 SGD$202 SGD$183 SGD
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Frequently Asked Questions

  • Where should I stay in New Canaan?

    Make yourself at home in New Canaan by choosing from our most frequently booked neighborhoods. We have over 520 vacation rentals in New Canaan, over 130 vacation rentals in Silvermine, and over 110 vacation rentals in Scotts Corners.

  • How much does it cost to stay in house rentals in New Canaan?

    Experience the best of New Canaan with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in New Canaan?

    Yes! Work meets play with ease at over 40 vacation rentals in New Canaan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in New Canaan?

    New Canaan has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in New Canaan?

    Four-legged friends are welcome in New Canaan. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Do house rentals in New Canaan have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in New Canaan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in New Canaan have wifi?

    Absolutely! We offer over 30 house rentals with wifi in New Canaan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in New Canaan have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in New Canaan. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in New Canaan

  • Total holiday rentals

    Explore 60 holiday rentals in New Canaan

  • Nightly prices starting at

    New Canaan holiday rentals start at $63 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of New Canaan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across New Canaan rentals

  • 4.8 Average rating

    New Canaan stays are highly rated by guests – averaging 4.8 out of 5!