Darien Vacations from $320

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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.
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $480, price is now $320 per person
$320
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,372 reviews)
Awesome Customer Service & clean room

Reviewed on Feb 24, 2026

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
Cranbury
Save 100% on your flight
Price was $717, price is now $502 per person
$502
per person
May 28 - Jun 2
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.4/10 Very Good! (1,086 reviews)
Clean basic rooms, Breakfast was good and chef this very courteous

Reviewed on Feb 28, 2026

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

2.5 out of 5
Save 100% on your flight
Price was $581, price is now $408 per person
$408
per person
May 28 - Jun 2
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.6/10 Excellent! (602 reviews)
Check in was great, smooth process. The room was ok, breakfast was good and location great. If I am ever in Ridgefield again I would consider staying here.

Reviewed on Feb 21, 2026

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Save 100% on your flight
Price was $559, price is now $399 per person
$399
per person
May 11 - May 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to White Plains (HPN)
6.2/10 (71 reviews)
Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford.

Reviewed on Jan 19, 2026

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
Save 100% on your flight
Price was $632, price is now $460 per person
$460
per person
May 28 - Jun 2
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
7.8/10 Good! (1,031 reviews)
Room and facilty were very clean and in good shape

Reviewed on Feb 28, 2026

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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 top-notch restaurants in this romantic 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
$133 nightly
The price is $152 total per night from Mar 8 to Mar 9
$152 total
Mar 8 - Mar 9
Total with taxes and fees
8.2/10 Very Good! (1,584 reviews)
The room was decent and clean. The beds were comfortable but they gave us small square pillows and only 3. Made it hard to get the pillows right. Breakfast was lackluster. The eggs were powdered and watery, the sausage was sitting in grease. No yogurts or breads but white bread. The coffee tasted ...

Reviewed on Mar 2, 2026

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
$186 nightly
The price is $212 total per night from Mar 29 to Mar 30
$212 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (1,293 reviews)
Staff was knowledgeable and helpful. Hotel rooms are clean and comfortable. The TV's in the rooms should be updated to SMART tv's to be able to stream services. I was there during a major blizzard and extended my stay and channels were very limited.

Reviewed on Mar 2, 2026

Sonesta White Plains Downtown
Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

2 out of 5
560 Saw Mill River Rd Ardsley NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Mar 5 to Mar 6
$126 total
Mar 5 - Mar 6
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
No hot water in the shower or sink in the bathroom. Called the front desk in the morning for assistance the phone cut off. The outlets at the head of the bed not working.

Reviewed on Mar 3, 2026

Ardsley Acres Hotel Westchester
See all 1,213 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 $320 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.