Darien Vacations from $262

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.
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
Ridgeway-Bullshead
Save 100% on your flight
Price was $393, price is now $262 per person
$262
per person
Nov 4 - Nov 7
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
7.8/10 Good! (544 reviews)
What a wonderful two nights stay at this beautiful hotel, incredibly clean quiet by far one of the best places I’ve stayed at!

Reviewed on Sep 30, 2025

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Save 100% on your flight
Price was $557, price is now $342 per person
$342
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,017 reviews)
The rooms are clean. The hotel smells great and the staff is awesome. The restaurant on site is delicious.

Reviewed on Sep 30, 2025

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Save 100% on your flight
Price was $568, price is now $391 per person
$391
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
8/10 Very Good! (1,178 reviews)
House keepercleanedroom when requested. Can’t get used to not having daily housekeeping. Guest has to request housekeeping just a new way of hotel management.

Reviewed on Sep 27, 2025

Delamar Southport

Delamar Southport

4 out of 5
Save 100% on your flight
Price was $1,384, price is now $1,005 per person
$1,005
per person
Nov 5 - Nov 11
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
9.4/10 Exceptional! (429 reviews)
Lovely inn and spa. What a relaxing gem!

Reviewed on Sep 24, 2025

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Price was $364, price is now $268 per person
$268
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.2/10 Very Good! (1,544 reviews)
Decent and affordable!

Reviewed on Oct 1, 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 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 top-notch restaurants in this romantic 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
$134 nightly
The price is $153 total per night from Oct 26 to Oct 27
$153 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (1,204 reviews)
"House keepercleanedroom when requested. Can’t get used to not having daily housekeeping. Guest has to request housekeeping just a new way of hotel management."

Reviewed on Sep 27, 2025

Hampton Inn White Plains/Tarrytown
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
$115 nightly
The price is $133 total per night from Oct 23 to Oct 24
$133 total
Oct 23 - Oct 24
Total with taxes and fees
8.4/10 Very Good! (1,670 reviews)
"The location and price was the reason for picking this hotel. I'm sure the owners will update the room when they can. Cute neighborhood. Lots of restaurants to choose from in a 20 min drive."

Reviewed on Oct 1, 2025

Amsterdam Hotel
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $95 total per night from Oct 26 to Oct 27
$95 total
Oct 26 - Oct 27
Total with taxes and fees
6.6/10 (848 reviews)
"My flight was delayed, so I didn’t arrived until 2:30am, the desk attendant was not there but a note that said to drop my key if I was checking out. After a short wait, I was checked in. This property will be much better in a couple of months, they are currently renovating."

Reviewed on Oct 1, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,168 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.

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 $262 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

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.