Darien Vacations from $188

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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 & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $296, price is now $188 per person
$188
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
16.4/10 Exceptional! (1,622 reviews)
The room was great - nice and clean! The free breakfast was awesome - great selection and really good food! The only downside was the pool was absolutely freezing. We were looking forward to using the pool every day....we only used it the first day for about 10 minutes because it was unbearable. That would be the only thing that could be better.

Reviewed on Nov 10, 2025

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Save 100% on your flight
Price was $381, price is now $244 per person
$244
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
16/10 Exceptional! (1,010 reviews)
Staff is friendly and professional!

Reviewed on Nov 7, 2025

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
Arlington
Save 100% on your flight
Price was $400, price is now $265 per person
$265
per person
Jan 27 - Feb 1
found 20 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
15.6/10 Exceptional! (472 reviews)
staff was very nice and everything was quiet and very clean. a quiet chilling vibe

Reviewed on Nov 10, 2025

Red Carpet Inn

Red Carpet Inn

2 out of 5
Cove - East Side - Shippan
Save 100% on your flight
Price was $407, price is now $275 per person
$275
per person
Jan 27 - Feb 1
found 20 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
12.8/10 Exceptional! (1,018 reviews)
EVERYTHING WAS GREAT

Reviewed on Nov 10, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $559, price is now $390 per person
$390
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
16/10 Exceptional! (1,010 reviews)
The room was great. But the staff were exceptional. Every encounter we had was great.

Reviewed on Nov 9, 2025

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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 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
$135 nightly
The price is $155 total per night from Nov 23 to Nov 24
$155 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,445 reviews)
Great experience can’t wait to come back

Reviewed on Nov 10, 2025

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $223 total per night from Dec 7 to Dec 8
$223 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (1,109 reviews)
Great location, friendly/helpful staff, spotless room…

Reviewed on Nov 9, 2025

Sonesta White Plains Downtown
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 Nov 30 to Dec 1
$145 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,258 reviews)
Very nice

Reviewed on Nov 9, 2025

Hampton Inn White Plains/Tarrytown
See all 1,181 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 $188 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.