Two wooden benches facing a calm body of water under a clear sky.

Darien Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Darien holiday rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (193 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is S$242
includes taxes & fees
18 Oct - 19 Oct
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is S$460
includes taxes & fees
20 Oct - 21 Oct
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is S$340
includes taxes & fees
29 Oct - 30 Oct
DUNE Fairfield Beach
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

4. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is S$646
includes taxes & fees
21 Oct - 22 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

5. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
The price is S$806
includes taxes & fees
21 Oct - 22 Oct
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

6. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is S$453
includes taxes & fees
16 Oct - 17 Oct
Elegant Hideaway with Free Parking
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

7. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is S$915
includes taxes & fees
21 Oct - 22 Oct
Luxury NYC Home Game Room Free Parking
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

8. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is S$1,895
includes taxes & fees
15 Nov - 16 Nov
Beechmont - Perfect for Family Retreat!
A breakfast buffet with pastries, fruits, and a coffee station.

9. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is S$1,474
includes taxes & fees
21 Oct - 22 Oct
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

10. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is S$1,409
includes taxes & fees
18 Oct - 19 Oct
Prime Luxe 3-BR NYC - Free Parking
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

11. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is S$1,419
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

12. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is S$1,184
includes taxes & fees
16 Oct - 17 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

13. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is S$1,043
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Darien Hotel Reviews

East Norwich Inn

East Norwich Inn

10/10 Excellent
"Nice quiet location and a clean room, make this a great getaway."
Jeff 1-night trip
Posted less than an hour ago
East Norwich Inn

Frequently asked questions

Can I find a holiday rental in Darien?

Yes, there are holiday rentals close to the most popular sights in Darien, or you can select a more secluded option if you're looking for a relaxing stay. Darien is known for its parks and shopping. Make sure you have time to check out the beaches and restaurants during your trip.

How many holiday rentals are there in Darien?

With 12 Expedia holiday rentals, you're guaranteed to find just the right place for your Darien stay.

What can I see and do in Darien?

Sleepy Hollow Park and Cove Island Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Woodway Park and The Mather Homestead.

What are holiday rentals like in Darien?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Darien. Holiday rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.