
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.
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Holiday rentals for every style
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Popular amenities for Darien holiday rentals
Other great holiday rentals in Darien
Guest favourite

Home in West Norwalk
4.96 out of 5 average rating, 50 reviewsModern Nature Retreat
MarkRating, 5 stars5 months ago
Beautiful house, great place for a relaxing weekend
Top guest favourite

Flat in Wall Street
5 out of 5 average rating, 63 reviewsPhoenix Engine #1
GrantRating, 5 stars3 weeks ago
Nathan’s a great host and he provided a great welcome pack. Great home for my wife and I and adult son. Plenty of space and walkable to coffee shops and river. Awesome communication and offered a very helpful relaxed late check out at no cost. Totally recommend this host and this property
Top guest favourite

Flat in Stamford
5 out of 5 average rating, 87 reviewsCozy King BR | Walk to beach | Close to downtown
JessicaRating, 5 stars1 week ago
Alexandra’s place was exactly as described in the listing and felt like home as soon as we arrived. Check in was easy and the house was easy to find. Alexandra also gave us some awesome local recommendations for food and drinks which was so thoughtful. Her responsiveness was amazing and greatly appreciated! If we’re ever back in the area, we’d absolutely come back again! Thanks for a wonderful stay!
Superhost

Guest house 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.
Top guest favourite

Guest house in East Norwalk
5 out of 5 average rating, 20 reviewsWaterfront Getaway - Norwalk, CT
HillaryRating, 5 stars1 week ago
Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.
Top guest favourite

Apartment in West Side
5 out of 5 average rating, 15 reviewsComfortable, Beautiful Apartment-Close to Downtown
KarenRating, 5 stars5 days ago
I am new to the Stamford / Greenwich area and needed a place to stay while I looked for a permanent residence. I stayed at Juan's place for about 3.5 months. It was very convenient to Greenwich (where I work) and to downtown Stamford (restaurants and shops) and the Stamford train station, which has great express trains to NYC. It is also very close to a grocery store and several gyms (I chose Orange Theory, only a few blocks away). I chose Juan's place for the location and king size bed. The bed was very comfortable, the towels were great and the overall unit worked really well for myself and my husband - it has wifi and we connected to our Netflix & other apps thru the smart TV. It fits two people comfortably and has a pull out sofa for guests (my college-age children visited a few times). The kitchen has what you need, including a dishwasher. There is one permanent parking space available and several guest spots. Juan was very responsive and a great host. Highly recommend!
Top guest favourite

Flat in South Norwalk
5 out of 5 average rating, 83 reviewsS. Norwalk Apt near the water!
LaurenRating, 5 stars4 days ago
It was our first time in Norwalk, and Michael’s and Lisa’s place was perfect for our visit. Extremely comfortable, pretty, and affordable, and walking distance to everything we wanted to do!
Guest favourite

Flat in Darien
5 out of 5 average rating, 19 reviewsCozy Jr. bedroom in Darien
DavidRating, 5 stars4 weeks ago
To use one word, Janeen’s place is AMAZING! Janeen and Joseph are amazing people and hosts! They are both very pleasant to speak with and extremely considerate and accommodating! Upon arriving, the place is superb. It is extremely clean and fresh with all very clean and new linens and towels. You immediately feel at home! This is especially the case with having hosts as thoughtful and considerate as Janeen and Joseph. It felt like we were staying with family, but with our own private space! Thank you again for the amazingly fresh baked bread! We will definitely be back!
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
- Rye Playland Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
- Central Park Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art