Darien Vacations from $714

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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.
Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Price was $916, price is now $714 per person
$714
per person
Sep 16 - Sep 20
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
8/10 Very Good! (1,005 reviews)

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Price was $1,110, price is now $778 per person
$778
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.

Reviewed on Jun 29, 2026

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was $3,046, price is now $2,285 per person
$2,285
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on Nov 8, 2025

Family Cottage with 4 King Beds

Family Cottage with 4 King Beds

2.5 out of 5
Historic District
Price was $1,242, price is now $949 per person
$949
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
President Donald J. Trump Intl. Airport (PBI) to White Plains (HPN)
No 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 $2,661, price is now $2,039 per person
$2,039
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
5.2/10 (9 reviews)

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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.
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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
$201 nightly
The price is $230 total per night from Aug 30 to Aug 31
$230 total
Aug 30 - Aug 31
Total with taxes and fees
Tarrytown House Estate
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
$188 nightly
The price is $215 total per night from Aug 30 to Aug 31
$215 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,336 reviews)
"Would like at least access to coffee 24hr. Wish the bar opened earlier. Maybe 4pm. All else was great."

Reviewed on Aug 5, 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
$178 nightly
The price is $205 total per night from Sep 6 to Sep 7
$205 total
Sep 6 - Sep 7
Total with taxes and fees
Hyatt Regency Greenwich
See all 1,205 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 $714 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.