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Darien Holiday Rentals

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Our top choices for Darien holiday rentals

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very good, (21)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is AU$223
includes taxes & fees
18 Dec - 19 Dec
The Mansion Hotel-style
9.4 out of 10, Exceptional, (8)
"The apartment was very clean with everything we needed for our stay. Outside noise was a little loud so I’d suggest a sound machine, but in case your forget the awesome host has supplied soft ear plugs for you. I would definitely visit again. "
United States
Chrystie
The price is AU$224
includes taxes & fees
18 Dec - 19 Dec
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is AU$439
includes taxes & fees
5 Jan - 6 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included

Holiday Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$224
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is AU$481
includes taxes & fees
18 Dec - 19 Dec
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
8.0 out of 10, Very good, (1)
"It was clean "
United States
Burton
The price is AU$442
includes taxes & fees
11 Jan - 12 Jan 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is AU$591
includes taxes & fees
18 Dec - 19 Dec
Marine Theme - 4 BR - Backyard - Fire pit
10.0 out of 10, Exceptional, (14)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$272
includes taxes & fees
21 Dec - 22 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AU$737
includes taxes & fees
11 Jan - 12 Jan 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (79)
"It was great"
United States
Natalie
The price is AU$191
includes taxes & fees
18 Dec - 19 Dec
Stamford Suites

Apartment in Westport

Spacious Studio with Pool Table
8.6 out of 10, Excellent, (7)
"So cute and comfortable "
United States
Maria
The price is AU$422
includes taxes & fees
18 Dec - 19 Dec
Spacious Studio with Pool Table
9.6 out of 10, Exceptional, (23)
"This was a great place! The host George and his wife were incredibly helpful and so nice, making the stay even better. I would absolutely recommend this spot to anyone and definitely plan to be back again!"
United States
Alexus C.
The price is AU$441
includes taxes & fees
7 Jan - 8 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
10.0 out of 10, Exceptional, (3)
"Nice little spot with a great host."
United States
J M.
The price is AU$250
includes taxes & fees
22 Dec - 23 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
The price is AU$2,415
includes taxes & fees
18 Dec - 19 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Apartment in Brooklawn - St. Vincent

Zen, Spacious & Comfy 2 bed, Lux beds
The price is AU$493
includes taxes & fees
18 Dec - 19 Dec
Zen, Spacious & Comfy 2 bed, Lux beds

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is AU$678
includes taxes & fees
18 Dec - 19 Dec
Luxury Designer 2 bedroom+office/3bed vacation home.
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is AU$587
includes taxes & fees
12 Jan - 13 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
3.0 star property
The price is AU$414
includes taxes & fees
22 Dec - 23 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Holiday Home in Brooklawn - St. Vincent

Centric property close to all the great things in the city
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
The price is AU$452
includes taxes & fees
18 Dec - 19 Dec
Centric property close to all the great things in the city
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

Find out more about Darien

Everything you need to know about Darien holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Darien holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darien holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Darien holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darien. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Darien holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darien holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Darien rentals

At Expedia, we put the best Darien holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Darien rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darien holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darien. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Darien has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday home rental outside of Darien is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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?

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

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.