House holiday rentals in Darien

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 · Parking

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 · Parking

Greenwich abode Close to Just about Everything

2 - Bedroom apartment in a duplex. 4 - Minutes to Greenwich Avenue Shopping 6 - Minutes to Port Chester restaurants 8 - Minutes to Rye town and restaurants. 5 - Minutes to The Capital Theater 5 - Minutes to Byram Beach 10- Minutes to Tod's Point Beach 4 - Minutes by car to Greenwich and Port Chester Metro North Station 1 - Twin Air Mattress, SERTA auto inflate, 15inch raised {UPON REQUEST } Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

Location · Family · Quiet

5BR Beach House, Water Views, Game Room, Backyard

Wake up to beautiful water views at this spacious 5-bedroom Stamford home, just a short walk from Cove Island Park and Beach. Enjoy a private backyard, game room, pool table, foosball and fire pit, with plenty of space for families and groups to relax, gather and have fun together. Spend your days by the beach or relaxing at home. Downtown Stamford, Metro-North, restaurants and shopping are all just a short drive away, offering the perfect mix of a peaceful coastal escape and city convenience.

Family · Location · Check-in

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.

Value · Location · Laundry

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 · Getting around

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.

Family · Location · Amenities

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.

Location · Family · Beach

Nautical Farm House on Working Farm with Animals

Completely renovated 3 bedroom home on working farm with fire place and piano. Lux kitchen features stainless steel appliances, Sub-zero refrigerator, and marble counters Private, fenced backyard with BBQ. Farm has goats, pigs, chickens, bee hives, ducks, and on-site cafe and bakery. Close to Huntington village, bike trails nature walks, restaurants, parks, and the beach. Fast wi-fi, laundry access and pet friendly. New beds and baby grand piano. Bedrooms have black out curtains.

Location · Family · Parking

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 · Value · Condition

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 · Value · Hospitality

Walkable Townhouse with Garage 45 min to NYC

Please add us to your wishlist for easy access, or message us if you have any questions! -Walk to Downtown Stamford -Free attached parking garage -Minutes from the train station, I-95, and hospital -Shared backyard for relaxing, grilling, or enjoying a quiet morning coffee A relaxing and worry-free stay just minutes from everything you need, ideal for families, business travelers, or long-term guests looking for comfort and convenience.

Location · Family · Comfort