Darien Vacations from $1,699

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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.
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,784, price is now $1,699 per person
$1,699
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
2/10 (1 review)
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,434, price is now $1,957 per person
$1,957
per person
Jun 12 - Jun 15
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1 review)
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was $5,908, price is now $3,543 per person
$3,543
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1 review)
Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

4 out of 5
Save 100% on your flight
Price was $4,588, price is now $2,780 per person
$2,780
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking

2 out of 5
Save 100% on your flight
Price was $4,588, price is now $2,780 per person
$2,780
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
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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 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

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

Darien Hotel Deals

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundable
$127 nightly
The price is $146 total per night from May 4 to May 5
$146 total
May 4 - May 5
Total with taxes and fees
EVEN Hotel Norwalk by IHG
Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike Westbury NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Apr 19 to Apr 20
$110 total
Apr 19 - Apr 20
Total with taxes and fees
8/10 Very Good! (1,430 reviews)
Third time i rent a room and no hot waterfor showers in the mor

Reviewed on Apr 17, 2026

Inn at Jericho
Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

4 out of 5
3998 Brush Hollow Rd Westbury NY
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Apr 27 to Apr 28
$170 total
Apr 27 - Apr 28
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
It was great

Reviewed on Apr 9, 2026

Viana Hotel and Spa, Trademark Collection by Wyndham
See all 1,209 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 $1,699 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.