Darien Vacations from $217

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.
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $298, price is now $217 per person
$217
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,264 reviews)
Clean room, quiet, fit the bill

Reviewed on Nov 27, 2025

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $566, price is now $373 per person
$373
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
Save 100% on your flight
Price was $818, price is now $546 per person
$546
per person
Jan 8 - Jan 15
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (1,002 reviews)
Room is great except the heating system doesn’t hold the temperature setting.

Reviewed on Dec 2, 2025

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
Crown Heights
Save 100% on your flight
Price was $382, price is now $273 per person
$273
per person
Jan 8 - Jan 12
found 9 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8.8/10 Excellent! (1,005 reviews)
More breakfast options.

Reviewed on Dec 2, 2025

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was $530, price is now $391 per person
$391
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
6.2/10 (71 reviews)
great place, always stay here when I am in Stamford.

Reviewed on Nov 22, 2025

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

Discover the most popular places to visit in Darien

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

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 top-notch restaurants and its entertainment choices.

Sleepy Hollow Park

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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $148 total per night from Dec 10 to Dec 11
$148 total
Dec 10 - Dec 11
Total with taxes and fees
8.2/10 Very Good! (1,475 reviews)
Comfortable and clean. In a good location off the highway and near the bridge. Great price for location!

Reviewed on Dec 1, 2025

Baymont by Wyndham White Plains - Elmsford
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
$136 nightly
The price is $156 total per night from Dec 10 to Dec 11
$156 total
Dec 10 - Dec 11
Total with taxes and fees
7.8/10 Good! (1,299 reviews)
Clean room, good amenities and great staff

Reviewed on Dec 1, 2025

Hampton Inn White Plains/Tarrytown
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Dec 21 to Dec 22
$113 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,020 reviews)
the staff and the rooms were great.

Reviewed on Nov 24, 2025

EVEN Hotel Norwalk by IHG
See all 1,185 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 $217 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.