House vacation rentals in New Canaan

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Value · Location · Cleanliness

The Cozy Little Cottage

Charming guest apartment 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, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.

Location · Family · Hospitality

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Value · Location · Accuracy

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Family · Value · Condition

Gem by the water+ firepit and all fenced backyard

An episode of The Curious Case of… was filmed right here at the property. Stay where the cameras rolled and experience the same atmosphere that caught the producers’ attention. One block away from the water & 3 blocks away from Dolphin Cove. Enjoy walking and site-seeing. 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. The house has also a lower-level unit.

Location · Family · Kitchen

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.

Family · Location · Decor

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Location · Value · Bathroom

Nature Retreat Airbnb

House located in beautiful and tranquil Redding, CT. Two floors with private deck. Main level: half-bath, cook's kitchen with a 4-person dining area, living room with flatscreen TV with an Apple TV and a view of nature. Living room convertible couch can sleep two small children or one adult. Upstairs: 2 bedrooms with full size beds, privacy blinds, bathroom w/ shower (no tub). If you want a getaway from the city, or just an escape then come to this quiet and private house in the woods.

Family · Value · Sleep quality

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Family · Location · Decor

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Seashell Bungalow - located in Stamford, just a stone's throw from NYC. Less than a 2-minute walk from the beach. Perfect for those looking to enjoy the tranquility of the beach with the city life nearby. Outdoor dining area - perfect for summer evening relaxation. Fully equipped for fun and adventure - paddle boards and various games available. Ideal for family vacations or a friends’ getaway. Book your stay today and enjoy an unforgettable beachside adventure!

Location · Family · Accuracy

Peaceful Light-Filled Guesthouse salt pool/sauna

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.

Value · Location · EV charging

New Beach Home near Stamford Downtown/Shippan

This spacious home in a desirable and serene residential neighborhood. Walking distance to West and Cummings Beaches, tennis /basketball courts, sport fields. The house is perfect for a large family or a corporate retreat. No parties or events allowed! If this property is booked for the dates you selected, click on the profile to see our other amazing properties in Stamford.

Value · Location · Condition