Darien Vacations from $287

Book a Hotel + Flight or Car together to unlock savings

Photo by Tim Rousseau

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Hilltop Inn & Suites

Hilltop Inn & Suites

2.5 out of 5
Northwest Yonkers
Save 100% on your flight
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
6.8/10 (316 reviews)
Renovations going on but clean safe and comfortable. I was delayed at airport got in late. They were waiting and happy to welcome me. Very nice place

Reviewed on Aug 11, 2025

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
Arlington
Save 100% on your flight
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip flight included
Tampa (TPA) to White Plains (HPN)
7.8/10 Good! (387 reviews)
Mice live in main building

Reviewed on Aug 15, 2025

The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Downtown Stamford
Save 100% on your flight
per person
Oct 29 - Nov 2
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
7.8/10 Good! (1,088 reviews)
Enjoy my stay each time

Reviewed on Aug 15, 2025

Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
6.8/10 (31 reviews)
Nice view from the apartment and great for business trip.

Reviewed on Dec 16, 2024

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Save 100% on your flight
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,092 reviews)
Room is clean Bed is comfortable Staff are friendly I’d stay here again

Reviewed on Aug 17, 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

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

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 top-notch restaurants 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

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
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,111 reviews)
"Location great for access to Tarrytown train. Clean and friendly."

Reviewed on Aug 14, 2025

Hampton Inn White Plains/Tarrytown
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
$144 nightly
The price is $164 total per night from Aug 24 to Aug 25
$164 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,394 reviews)
"N/A"

Reviewed on Aug 9, 2025

Baymont by Wyndham White Plains - Elmsford
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $143 total per night from Aug 24 to Aug 25
$143 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,285 reviews)
"Very pleasant, professional front desk attendants. Beautiful facility, well maintained. A pleasure to stay there."

Reviewed on Aug 14, 2025

Norwalk Inn & Conference Center
See all 1,135 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.

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 $287 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.