Darien Vacations from $672

Book a Hotel + Flight or Car together to unlock savings

Photo by Tim Rousseau

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.
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $994, price is now $672 per person
$672
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
6.8/10 (3 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 2026

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $1,207, price is now $703 per person
$703
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
2/10 (3 reviews)
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,289, price is now $1,376 per person
$1,376
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
3/10 (4 reviews)
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,139, price is now $2,135 per person
$2,135
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
5.6/10 (8 reviews)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar 17, 2024

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $1,661, price is now $1,154 per person
$1,154
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
2/10 (1 review)
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Discover the most popular places to visit in Darien

Sleepy Hollow Park

Sleepy Hollow Park is just one of the places to see in Darien, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its entertainment choices.

Sleepy Hollow Park

Sapelo Island Visitors Center

After visiting Sapelo Island Visitors Center, make a plan to see the other sights and activities in Darien. Discover the area's lively bars and its entertainment choices.

Sapelo Island Visitors Center

McGuane Field

After visiting McGuane Field, make a plan to see the other sights and activities in Darien. Check out the shops and lively bars in this family-friendly area.

McGuane Field

Darien Hotel Deals

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundable
$131 nightly
The price is $151 total per night from Jun 21 to Jun 22
$151 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (1,131 reviews)
"Quiet stay, clean room, good breakfast , close the highway and restaurants, would stay again"

Reviewed on Jun 3, 2026

EVEN Hotel Norwalk by IHG
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $226 total per night from Jun 14 to Jun 15
$226 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (1,325 reviews)
"Excellent service"

Reviewed on May 31, 2026

Sonesta White Plains Downtown
Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike Westbury NY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Jun 10 to Jun 11
$118 total
Jun 10 - Jun 11
Total with taxes and fees
8/10 Very Good! (1,535 reviews)
"Too much noise"

Reviewed on Jun 4, 2026

Inn at Jericho
See all 1,190 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

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Frequently asked questions

How much does a Darien vacation package cost?
Offering excellent value package deals from $672 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.