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New Canaan places to stay

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Top-rated places to stay in New Canaan

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guesthouse in Wilton

4.96 out of 5 average rating, 112 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Guest suite in Wilton

4.89 out of 5 average rating, 133 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…

Guesthouse in Rowayton

4.99 out of 5 average rating, 135 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Guest suite in Norwalk

4.9 out of 5 average rating, 138 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

Rental unit in Redding

4.94 out of 5 average rating, 476 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your HOLIDAY getaway to the Huckleberry Quarters, a totally renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A perfect HOLIDAY getaway, writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Guest suite in Wilton

4.84 out of 5 average rating, 128 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.

Cottage in South Salem

4.95 out of 5 average rating, 222 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 :)

Home in Pound Ridge

5 out of 5 average rating, 149 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. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Rental unit in Stamford

4.87 out of 5 average rating, 135 reviews

Stamford Guest Suite - This is a NO Smoking unit

1 bedroom, 1 bathroom, and large Living room and kitchen set in a wooded setting. Private entrance and off street parking. The suite is for max 2 person. There is a separate fold out twin bed in the Living Room. There is a desk for working. Nice patio with outdoor grill. Coffee maker & makings for a good cup of coffee. NO Smoking unit.

Guesthouse in Bedford

4.92 out of 5 average rating, 194 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Home in Stamford

4.99 out of 5 average rating, 154 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.

Guesthouse in South Salem

4.94 out of 5 average rating, 265 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Vacation rentals for every style

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Unique stays

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Popular amenities for New Canaan places to stay

Laptop-friendly workspace

Air conditioning

Stay near New Canaan's top sights

Grace Farms31 locals recommend

The Glass House27 locals recommend

Stamford Museum & Nature Center26 locals recommend

ACME Markets17 locals recommend

Trader Joe's15 locals recommend

Waveny Park12 locals recommend

Other great vacation rentals in New Canaan

Home in Pound Ridge

4.89 out of 5 average rating, 37 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

Rental unit in Stamford

5 out of 5 average rating, 65 reviews

Cozy King BR | Walk to beach | Close to downtown

Home in Norwalk

5 out of 5 average rating, 33 reviews

Magical Holidays: Norwalk/Westport, Tree & Cheer!

Home in Darien

4.8 out of 5 average rating, 182 reviews

Convenient and Cozy Antique Cape

Home in Katonah

5 out of 5 average rating, 13 reviews

The Cottage at Fern Hill

Home in South Norwalk

4.96 out of 5 average rating, 53 reviews

Chic Historic Home w/Water View

Guesthouse in Wilton

5 out of 5 average rating, 37 reviews

The Ciderhouse Cottage - private escape in Wilton

Rental unit in South Norwalk

5 out of 5 average rating, 68 reviews

S. Norwalk Apt near the water!

Quick stats about vacation rentals in New Canaan

Total rentals
40 properties
Total number of reviews
850 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

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 110 vacation rentals in Silvermine, and over 240 vacation rentals in West Norwalk.
Are there house rentals with a dedicated workspace in New Canaan?
Yes! Work meets play with ease at over 10 house rentals in New Canaan featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in New Canaan?
New Canaan has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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 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.
Are there pet-friendly house rentals in New Canaan?
Four-legged friends are welcome in New Canaan. Choose from more than 10 house rentals for guests traveling with pets.
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.
What are the most popular amenities for House Rentals in New Canaan?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore