
House holiday rentals in Darien
Find and book unique houses on Airbnb
Top-rated house rentals in Darien
Guests agree: these houses are highly rated for location, cleanliness and more.

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!

Luxurious Barn With New England Charm
Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.
THE OASIS @ LONG ISLAND
A true home away from home that sits right in the heart of Huntington NY with shops, cafes and entertainment all within 10 minutes in either direction and Manhattan just a 50 minute drive away. The house is immaculately presented and offers guests all the comforts of home including a stocked fridge filled with complimentary drinks and a fully stocked coffee bar. Watch the world go by out of the two large bay windows or watch the sunset from your own private balcony. Come and enjoy the Oasis.

The ARLO - Walk to Brewery & Restaurants
Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

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.

Peaceful Suburban Colonial w/New Kitchen.
Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

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.

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.

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. 36 - minutes to NYC 1 - Twin Air Mattress, SERTA auto inflate, 15 inch raised { UPON REQUEST } 4 - Minutes Uber/Lyft drive to Greenwich and Port Chester Metro North Station Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

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.

Stylish Beach Home near Downtown/Cove Beach
This spacious 5 bedroom home with water views and a lot of natural light tucked away in a quiet and serene residential neighborhood. The house is perfect for a large family or a corporate retreat. If this property is booked for the dates you selected, click on the profile to see our other amazing properties in Stamford.

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.
Popular amenities for house rentals in Darien
House rentals with a pool

Joyful Beach House, viewing The Great South Bay

Private Hudson Valley Country Retreat

Entire Home (private pool), Event Friendly

Gameroom, backyard + pool! 7m to train + downtown

Midcentury Modern ZenHouse Sculptor Studio

Spacious 4 bedroom, oasis with ocean views galore

Port Jefferson Convenient, Cozy and Chic!

Gorgeous Waterfront and Indoor Pool Family Oasis!
Weekly house rentals

5 Minute Walk to Beach & Downtown Fairfield

Family friendly

Westport Border | 4 br | Fenced Backyard | Parking

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Chic Historic Home w/Water View

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Stareway to Heaven

L'il in town Gem
Private house rentals

Cozy&Chic 1Bd in Greenwich | Designer Stay near NY

Charming Coastal Hideaway Near the Shore

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

Spacious Home - Center Of Stamford

Newly renovated modern private guest wing

Still Stays - 3BR Ranch Near Westport & Fairfield

Elegant Hideaway: Cozy Cottage in Katonah, NY

Comfortable Mid-Century on Quiet Country Road
When is the best time to visit Darien?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $283 SGD | $283 SGD | $283 SGD | $229 SGD | $255 SGD | $240 SGD | $243 SGD | $236 SGD | $223 SGD | $255 SGD | $283 SGD | $283 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about house rentals in Darien

Total holiday rentals
Explore 30 holiday rentals in Darien

Verified guest reviews
Over 720 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
20 properties have a dedicated workspace

Wifi availability
30 of Darien holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Darien rentals

4.8 Average rating
Darien stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Columbia University
- Yale University
- Central Park Zoo
- MetLife Stadium
- Jones Beach
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Empire State Building
- Grand Central Terminal
- Statue of Liberty
- Rye Beach
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- The Metropolitan Museum of Art
- Gilgo Beach
- Astoria Park
- Robert Moses State Park




