Darien Vacations from $442

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Darien Vacation

Lock in a Darien vacation package that has only the things you need and nothing you don't. Great for history, bars and pubs and dining, consider basing yourself in the neighborhood of Downtown Stamford. Love to explore your new surroundings? Chelsea Piers, The Glass House and Norwalk Maritime Aquarium are some of the most popular places to visit during a trip to Darien. Check out Expedia's wide range of travel options and start organizing your ultimate vacation to Darien today.

The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $558, price is now $442 per person
$442
per person
Jan 15 - Jan 18
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.8/10 Excellent! (1,193 reviews)

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

4 out of 5
Price was $2,156, price is now $1,567 per person
$1,567
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
2/10 (3 reviews)
It was a scam the house was never a villa and someone lives there they lied and are scammers

Reviewed on Oct 25, 2026

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC

2 out of 5
Bryn Mawr
Price was $1,282, price is now $1,018 per person
$1,018
per person
Dec 11 - Dec 16
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Safe location, looks newly restored. Neighbors upstairs they’re terrible walking all night and loud talking

Reviewed on Oct 27, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was $1,227, price is now $975 per person
$975
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)

Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

2 out of 5
Price was $776, price is now $630 per person
$630
per person
Dec 18 - Dec 23
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
7.4/10 Good! (1,013 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Darien
View all trips

Stay near popular Darien attractions

Woodland Park

This 64.7-acre sanctuary offers serene trails winding through diverse ecosystems and past two tranquil ponds. Bring binoculars to spot turtles, frogs, and waterfowl while exploring historic stone walls and footbridges.
See properties

Darien Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $218 total per night from Nov 1 to Nov 2
$218 total
Nov 1 - Nov 2
Total with taxes and fees
Tarrytown House Estate
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
$148 nightly
The price is $165 total per night from Nov 1 to Nov 2
$165 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (1,813 reviews)
"Very bad customer services & inhuman hotel polises"

Reviewed on Oct 28, 2026

East Norwich Inn
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
$301 nightly
The price is $346 total per night from Nov 29 to Nov 30
$346 total
Nov 29 - Nov 30
Total with taxes and fees
J House Greenwich
See all 1,203 properties in Darien
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.

Find the Best Darien Vacation Packages

Darien Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
20,700
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Norwalk Maritime Aquarium, Compo Beach and The Maritime Aquarium

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Darien vacation package cost?
Offering excellent value package deals from $442 on Expedia, you'll be surprised at how little a vacation to Darien costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Darien?
December, January and February are great times to look for cheap Darien vacation packages. Opting to travel in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Darien?
The ideal length of your Darien vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to tick off all the leading sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Darien?
Well known for its views, coastal beaches and golfing, a Darien vacation has something for everyone. Be sure to check out major sights like Sleepy Hollow Park and Sapelo Island Visitors Center, and consider renting some wheels for day trips to discover even more.
How to find the best Darien package deals?
Landing a cheap Darien package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Darien package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Darien vacation as a package?
You can enjoy significant savings on your next Darien getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Darien?
Land incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Darien getaway.
Does Expedia offer Book Now, Pay Later Darien vacation packages?
Secure your perfect trip to Darien with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next paycheck — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up cheap deals before they disappear.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.