
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.
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Popular amenities for Darien holiday rentals
Other great holiday rentals in Darien

Apartment in Stamford
4.83 out of 5 average rating, 53 reviewsBeautifully Renovated 1Bd near Quingley/Cove Beach
RossyRating, 5 stars2 weeks ago
Thank you Jessy beautiful place.
Guest favourite

Guesthouse in Stamford
4.93 out of 5 average rating, 44 reviewsCarriage house flat near beach
SaraRating, 5 stars4 days ago
Christine was very welcoming and I very much enjoyed my stay! The carriage house apartment was even more spacious and attractive than in the photos. We also appreciated the helpful messages we received. This accommodation is definitely worth the price!
Superhost

Guesthouse in Rowayton
4.95 out of 5 average rating, 19 reviewsAdorable 1-Bedroom Guest Cottage in Rowayton
CaseyRating, 5 stars9 months ago
A lovely experience! Blythe had great local tips which helped make our stay even more special. Super charming space and great neighborhood.

Home in Norwalk
4.96 out of 5 average rating, 47 reviewsTake Time Out… In A Water Community, Norwalk, CT
JosephRating, 5 stars1 month ago
Great stay and highly recommended. A typical New England style house with the charm and quirks that come with it. I would never say not to stay here but to make sure you are a good fit for the home. We should have paid closer attention as our toddler had to be watched like a hawk. This is in no way the house or owners fault. Beyond that 13/10, amazing location, all walkable, and a fantastic quiet community. Our child loved the park that was one block away and the dad's loved the location being so close the NHRL robot combat facility. Great beach community and quiet enough to sleep with the windows open and enjoy the breeze.
Top Guest favourite

Apartment in Stamford
4.97 out of 5 average rating, 176 reviewsStandalone Cottage surrounded by woods
ChristineRating, 5 stars4 days ago
Paul was so incredibly kind and good with communication. He gave clear instructions and everything was as expected. Such a wonderful and serene property and area. He provides such intricate details. I had a towel that was so incredible soft and looked brand new, he gave me soaps and a loofah, he provides toothpaste and he ever had jars with hair ties, cotton rounds, qtips, etc.!! Hello, talk about details!! He had a snack bar with yummy options and complimentary wine!! If you are looking for a place in Greenwich look no further! Thank you so much Paul for such an incredible stay! I hope to be back! :)

Apartment in Stamford
4.93 out of 5 average rating, 42 reviewsSpacious. Water Views & Access. Steps to Beach.
DeniseRating, 5 stars2 weeks ago
Excellent host, fabulous location. Our stay was amazing with excellent amenities. The bed was amazing so comfortable and a very peaceful location right next to Cove Beach. Everything was as described. A truly lovely apartment and everything we needed… and with parking. Can’t wait to stay again. Loved the tranquil garden and loved watching the birds and squirrels. We cannot say how much we enjoyed our stay….absolutely excellent.
Top Guest favourite

Apartment in Fairfield
5 out of 5 average rating, 16 reviewsNew & Modern Studio Apartment in Fairfield
Anne EliseRating, 5 stars3 days ago
Julie’s place is lovely, VERY clean with gorgeous new appliances. Bed was very comfortable. The space is quite large, in the basement of their home. She is an excellent communicator, everything went smoothly. Would stay here again!
Guest favourite

Apartment in Stamford
4.82 out of 5 average rating, 68 reviewsSuburban Apartment in Stamford
LataviaRating, 5 stars15 months ago
Clean and simple place the pics definitely don’t do it justice! Highly recommend!
Quick stats about holiday rentals in Darien
Total rentals
50 properties
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art