Darien Holiday Rentals

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Our top choices for Darien holiday rentals

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (96 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
The price is AU$213
includes taxes & fees
15 Feb - 16 Feb
Stamford Suites

DUNE Fairfield Beach

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

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$586
includes taxes & fees
2 Feb - 3 Feb
Guesthouse at Norwalk Inn

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is AU$409
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"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$412
includes taxes & fees
1 Feb - 2 Feb
Renovated 2BR Retreat / Modern Comforts Included

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"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$608
includes taxes & fees
5 Feb - 6 Feb
Luxury Designer 2 bedroom+office/3bed vacation home.

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"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$447
includes taxes & fees
1 Feb - 2 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is AU$304
includes taxes & fees
4 Feb - 5 Feb
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful "
United States
Nolufefe Z.
The price is AU$502
includes taxes & fees
1 Feb - 2 Feb
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is AU$965
includes taxes & fees
4 Feb - 5 Feb
Luxury NYC Home with Free Parking for 12

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (17 reviews)
"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$261
includes taxes & fees
1 Feb - 2 Feb
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is AU$409
includes taxes & fees
8 Feb - 9 Feb
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is AU$347
includes taxes & fees
8 Feb - 9 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is AU$1,104
includes taxes & fees
2 Feb - 3 Feb
Luxury NYC Home Game Room Free Parking

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (26 reviews)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is AU$669
includes taxes & fees
1 Feb - 2 Feb
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is AU$604
includes taxes & fees
11 Feb - 12 Feb
Marine Theme - 4 BR - Backyard - Fire pit

The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8 reviews)
"Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay."
United States
George M.
The price is AU$955
includes taxes & fees
1 Feb - 2 Feb
The B&W Haven 5BR Home with yard theater + Office

The Gallery in Downtown Stamford

The Gallery in Downtown Stamford
Downtown Stamford
10.0 out of 10, Exceptional, (5 reviews)
"Another great experience at this beautiful property"
United States
Jeffrey W.
The Gallery in Downtown Stamford

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Greenwich
10.0 out of 10, Exceptional, (1 review)
"The location was perfect for our family getaway. The snow and river backdrop brought the holiday spirit out in our college age kids. There was plenty of room and the fireplace was great. All the appliances are high end and the communication was excellent. The host went out of his way to make the visit special. Would highly recommend "
United States
Scott and Linsay T.
The price is AU$1,502
includes taxes & fees
8 Feb - 9 Feb
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"The house is adorable and very clean. The beds are very comfortable.Everything was set up perfectly. The location and views are great. I would definitely stay here again. "
United States
Kerry P.
The price is AU$652
includes taxes & fees
2 Feb - 3 Feb
Captain's Cottage - Cold Spring Harbor Water Views
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$213 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?

Waterfront Retreat Center for Health & Wellness: This holiday home rental outside of Darien is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Woodway 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 Valley Street Open Space.

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.