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, 365 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 bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.
Home in East Norwalk
4.98 out of 5 average rating, 123 reviews

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

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, 172 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…

Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guest house in Waccabuc
4.98 out of 5 average rating, 131 reviews

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Top guest favourite
Home in Wilton
4.97 out of 5 average rating, 147 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
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 210 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top guest favourite
Flat in South Norwalk
4.99 out of 5 average rating, 123 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 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, 126 reviews

A Lovely Cottage in the Woods (Pool Open May 8!)

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 well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.
Home in Stamford
4.83 out of 5 average rating, 205 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Superhost
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
4.81 out of 5 average rating, 272 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.

Top guest favourite
A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.
Cottage in South Salem
4.96 out of 5 average rating, 265 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 :)

Top guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge
5 out of 5 average rating, 180 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna.. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Popular amenities for New Canaan holiday rentals

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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 490 vacation rentals in New Canaan, over 120 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 30 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 10 vacation rentals for guests traveling with pets.

  • Do house rentals in New Canaan have air conditioning?

    Absolutely! We offer over 20 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 20 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 50 holiday rentals in New Canaan

  • Nightly prices starting at

    New Canaan holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 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!