Darien Vacations from $345

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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.
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $518, price is now $345 per person
$345
per person
Aug 13 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
8.2/10 Very Good! (1,129 reviews)
Loved it! We hope to be back soon!

Reviewed on Jul 2, 2026

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 $3,092, price is now $1,978 per person
$1,978
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
3/10 (4 reviews)

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 $746, price is now $506 per person
$506
per person
Aug 13 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
6.8/10 (3 reviews)

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Price was $591, price is now $445 per person
$445
per person
Aug 13 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
8/10 Very Good! (1,002 reviews)
The walls are paper thin, we heard every door slam shut, people in the hallways, very hard time sleeping. Housekeeping came at 9:30 am, I answered the door and the lady saw that i was half asleep and kind of walked away. Security knocked on our door to let us know if we didn’t want to be bothered, have the sign up of do not disturb. I was confused because we literally checked in the night before and didn’t expect housekeeping to come already. I also did not say one word to the housekeeping lady or caused an issue so i don’t get why security had to come and say something. We also got charged for the parking garage that we DID NOT use because it was full. We explained it at check out and they still charged us THEIR price versus the other parking garage even though the other parking garage was cheaper. We will not be staying here ever again.

Reviewed on Jun 28, 2026

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Price was $784, price is now $604 per person
$604
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to White Plains (HPN)
8.6/10 Excellent! (1,154 reviews)
Everything is great this Hotel as a pool great food at the restaurant rooms are clean. Staff are very friendly and helpful.

Reviewed on Jul 2, 2026

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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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $129 total per night from Jul 26 to Jul 27
$129 total
Jul 26 - Jul 27
Total with taxes and fees
8/10 Very Good! (1,536 reviews)
"Out dated property with 70th feel with very limited breakfast choices. Needs room renovation."

Reviewed on Jun 30, 2026

Hampton Inn White Plains/Tarrytown
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
$195 nightly
The price is $223 total per night from Jul 26 to Jul 27
$223 total
Jul 26 - Jul 27
Total with taxes and fees
8.8/10 Excellent! (1,324 reviews)
"Beautifully clean and comfortable"

Reviewed on Jul 1, 2026

Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $216 total per night from Jul 26 to Jul 27
$216 total
Jul 26 - Jul 27
Total with taxes and fees
8.6/10 Excellent! (1,041 reviews)
"Book this Hyatt hotel, you’ll be happy you did. Everything is great including the food and accommodations to the people who work there. Excellent."

Reviewed on Jun 30, 2026

Hyatt Regency Greenwich
See all 1,169 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 $345 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.

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