Darien Vacations from $676
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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.
Modern Comfort in the Heart of NYC
Southeast Yonkers
$676
per person
Dec 11 - Dec 14
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Luxury NYC Home with Free Parking for 12
$881
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.
Reviewed on Feb 11, 2026
Luxury NY Home with Free Parking
$2,776
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) to White Plains (HPN)
8/10 Very Good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.
Reviewed on Nov 8, 2025
Modern Luxury Home w GameRoom & Parking
Southeast Yonkers
$2,913
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
5/10 (12 reviews)
Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ...
Will use this management and property owner in our upcoming short terms rentals.....
Reviewed on Sep 13, 2026
Stay near popular Darien attractions
Woodland Park
This 64.7-acre sanctuary offers serene trails winding through diverse ecosystems and past two tranquil ponds. Bring binoculars to spot turtles, frogs, and waterfowl while exploring historic stone walls and footbridges.
Sleepy Hollow Park
Sleepy Hollow Park offers a tranquil pond where visitors can observe native turtles and diverse bird species. Bring binoculars for the best wildlife viewing experience along the peaceful walking paths.
McGuane Field
McGuane Park's meticulously maintained baseball fields serve as the heart of Darien's Little League community. Visitors can enjoy playfields, a playground, and indoor batting cages while watching youth sports in action.
David Fetter Park
David Fetter Park offers 1.7 acres of lush greenery and well-maintained paths for peaceful outdoor recreation in Darien. Visitors can escape urban life with refreshing strolls or runs along its scenic trails.
Valley Street Open Space
You can take time to visit Valley Street Open Space during your travels to Darien. Amble around the area's parks or visit its shops.
The Mather Homestead
Revolutionary War-era homestead of Stephen Mather, first National Park Service director. Explore original 18th-century furnishings and learn about early American conservation on guided tours.
Darien Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Oct 4 - Oct 5
Total with taxes and fees
Inn at Jericho
101 Jericho Turnpike Westbury NY
Fully refundableReserve now, pay when you stay
$82 nightly
$92 total
Oct 28 - Oct 29
Total with taxes and fees
8/10 Very Good! (1,842 reviews)
"Excellent location and extremely clean"
Reviewed on Sep 28, 2026
Westchester Marriott
670 White Plains Rd Tarrytown NY
Fully refundableReserve now, pay when you stay
$195 nightly
$223 total
Oct 4 - Oct 5
Total with taxes and fees
9/10 Wonderful! (658 reviews)
"Awesome hotel"
Reviewed on Sep 28, 2026
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 $676 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
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- Visit Bridgeport
- Visit Darien
- Stamford Public Library - Ferguson Library
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- Hand & Stone Massage and Facial Spa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
