
Holiday houses in Darien
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Top-rated holiday rentals in Darien
Guests agree: these stays are highly rated for location, cleanliness and more.

Costal Coziness: 1BR Retreat near beach.
Welcome to your cozy private getaway, nestled within a charming multifamily home just a short walk away from the beach. This delightful one-bedroom unit offers a serene retreat for your beachside escape. Relax in the spacious living room, complete with a comfortable seating area and a convenient kitchenette. The queen-size bed in the private bedroom ensures a peaceful night's sleep. Embrace the coastal vibes and enjoy the convenience of beachside living in this inviting and well-appointed unit.

Sugar Shack Studio | Downtown Skyline Views
Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!

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.

Luxurious 1BR Downtown Stamford
Step into your luxurious haven in the heart of downtown Stamford, where opulence seamlessly meets comfort and indulgence becomes your personal mantra. From the impeccable design and luxurious amenities to the prime location, every moment spent here is a celebration of the finer things in life. Treat yourself to an extraordinary stay, crafting memories that will linger in your heart for a lifetime . Welcome to a world where luxury knows no bounds, and warm hospitality eagerly awaits your arrival

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.

Romantic, Cozy and Private, 1 Block from Beach
Relax in your private romantic retreat with Canopy Queen Bed & Beautiful modern bathroom, 1 Block from beach, Second floor studio with small fridge, microwave, coffee maker, induction cook top, SmartTV... Just 7 min from the Long Island Railroad, Oyster Bay stop. Near to restaurants, shops, tennis courts. You can go biking, swimming, fishing, play golf, rent kayaks, motor boats, paddle boards. Visit Arboretums, Historic sites, Parks, walk along the water, go to the nearby movies and more...

1BR full cottage, 1 min walk to private beach
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 and dog friendly town; you don't even need a car while here.

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.

Convenient and Cozy Antique Cape
Adorable little house in Darien CT, with a fireplace in winter and the beautiful local beaches in the summer. Right across from Trader Joe’s and around the corner from route 1 and Interstate 95, the little house is super convenient to local amenities. Probably the best perk of its central location is that it’s nestled behind Rorys, the best pub ever, so there’s no need to even cook if you are too busy or just don’t want to after working all day or a long day at the beach

A Lovely Cottage in the Woods
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.

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.

Spacious. Water Views & Access. Steps to Beach.
Spacious apartment with King Size Bed. Direct access to Cove Pond & Long Island Sound. Easy access to downtown Stamford, Stamford Train Station & Manhattan. A few steps away from Cove Island Beach & Park. Apartment features high ceilings, central heating & cooling, brand new washer & dryer, hardwood floors, formal dining room and 60" HDTV with Amazon Fire TV. Guests have complimentary access to YouTube TV (comparable to cable), Peacock, & Prime Video.
Popular amenities for Darien holiday rentals
Other great holiday rentals in Darien

Sun Room

Solo travelers: cozy room, water view, own bath.

Quiet room in the heart of Westchester

Stamford Bohemian by HarborPoint, Downtown &Train

Hotel-Style Mansion w/ Private Suites (Room 1/Spa)

Cos Cob, Greenwich garden studio

Cozy Room #2 | New Rochelle | Near NYC

Lovely-Private Room with private bathroom &parking
When is the best time to visit Darien?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 AUD | $209 AUD | $233 AUD | $228 AUD | $234 AUD | $240 AUD | $230 AUD | $210 AUD | $197 AUD | $210 AUD | $234 AUD | $204 AUD |
| 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 |
Frequently Asked Questions
Where should I stay in Darien?
Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 300 vacation rentals in Noroton Heights, over 250 vacation rentals in West Norwalk, and over 470 vacation rentals in Tokeneke.
Are there vacation rentals with a dedicated workspace in Darien?
Yes! Work meets play with ease at over 30 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Darien?
Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there Darien vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Darien, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Darien have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Darien have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Darien?
Darien has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Darien?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Darien

Total holiday rentals
Explore 60 holiday rentals in Darien

Verified guest reviews
Over 1,580 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Darien holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Darien rentals

4.8 Average rating
Darien stays are highly rated by guests—averaging 4.8 out of 5!
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library - Bloomingdale Library
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Jones Beach
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Radio City Music Hall
- Statue of Liberty
- Canarsie Beach
- Rye Beach
- USTA Billie Jean King National Tennis Center
- McCarren Park
- The Metropolitan Museum of Art
- Astoria Park




