
Holiday rentals 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.

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.

Norwalk/Westport Border, Near Calf Pasture Beach
Welcome to Norwalk Retreat. A beautifully designed 4-bedroom home crafted for your ultimate comfort. Perfect for families and friends, this property offers an array of amenities to ensure a memorable stay. Located on the Norwalk/Westport border, just 60 minutes to NYC. Local Attractions: •Minutes to Calf Pasture Beach •SoNo District: Enjoy the vibrant nightlife, boutique shopping, and an array of dining options •Experience kayaking and paddleboarding on the picturesque Norwalk River

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

Waterside
Why would anyone want to stay in a hotel when you can stay right on the river. With a stunning view of the Five Mile River, accompanied with a peaceful outside private patio, this unit is within walking to everything in Rowayton. It is had a fully equipped kitchen, high-end appliances and a super comfortable, inclining Queen bed to adjust to watching the large screen TV. There is also a communal larger graveled area with Adirondack chairs for you to enjoy the sunsets.

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.

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.

Cozy Jr. bedroom in Darien
Nestled between Rowayton and Darien’s beaches, this one-bedroom retreat offers a perfect getaway from the bustling city life. As you step into your private entrance of this thoughtfully designed apartment, you will feel a sense of comfort and tranquility. The open floor plan seamlessly combines the living, dining, and kitchen areas. Whether you are visiting for business or pleasure, a good night's sleep awaits you on the Wink king sized bed.
Popular amenities for Darien holiday rentals
Other great holiday rentals in Darien

Beautifully Renovated 1Bd near Quingley/Cove Beach

Charming Cottage Near Beach/Town

Cozy room with shared bathroom

Adia's Home

Brook Haven Home away from home!

Private entrance, private bathroom, quiet zone.

Sunshine Room by harbor downtown beach, I-95&Train

The Perch, a luxe cottage in the woods 1h from NYC
When is the best time to visit Darien?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £138 | £104 | £116 | £114 | £117 | £120 | £114 | £105 | £98 | £105 | £117 | £102 |
| 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 250 vacation rentals in West Norwalk, over 300 vacation rentals in Noroton Heights, 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 house rentals in Darien have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Darien have wifi?
Absolutely! We offer over 30 house 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 Apartment Rentals in Darien?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
50 of Darien holiday rentals include wifi 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
- Yale University
- MetLife Stadium
- Jones Beach
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Statue of Liberty
- Radio City Music Hall
- Canarsie Beach
- USTA Billie Jean King National Tennis Center
- Rye Beach
- The Metropolitan Museum of Art
- Gilgo Beach
- Astoria Park




