Darien Vacations from $718
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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
- Delamar Greenwich Harbor
Jan 14 - Jan 17Delamar Greenwich Harbor + Flight
Greenwich3 nights4.0 star property9.4/10 - Exceptional (1,000 reviews)"our room was just okay not worth the money. The walls are paper thin could hear our neighbors full conversation at 6am. When we mentioned it to the front desk they could have cared less."Reviewed November 1, 2026Roundtrip • Orlando (MCO) - White Plains (HPN)MCO - EWR • Nonstop LGA - MCO • Nonstop$926$718found 1 day agoper traveler - 3BR Prime Luxury NY - Free Parking
Jan 18 - Jan 233BR Prime Luxury NY - Free Parking + Flight
White Plains5 nights2.0 star property6.0/10 - (1 review)"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."Reviewed March 30, 2026Roundtrip • Orlando (MCO) - White Plains (HPN)MCO - HPN • 1 stop HPN - MCO • Nonstop - The Stamford Hotel
Dec 16 - Dec 20The Stamford Hotel + Flight
Downtown Stamford4 nights3.5 star property8.0/10 - Very good (1,258 reviews)"The hotel advertises breakfast to order for a fee however there is no such service and this was the main reason i booked this particular hotel, been in a business trip this was a most so that I didn’t have to worry about find it a place before heading out."Reviewed November 6, 2026Roundtrip • Dallas (DFW) - White Plains (HPN)DFW - HPN • 1 stop HPN - DFW • 2 stops$1,070$814found 1 day agoper traveler - Tarrytown House Estate
Jan 18 - Jan 23Tarrytown House Estate + Flight
Tarrytown5 nights3.5 star property8.2/10 - Very good (1,423 reviews)"It wasn’t worth 400$ a night plus 130$ dog fee. More like a 220$ a night room with a 50$ dog fee. The venue was nice but the room was just a holiday inn room. Older carpet , metal spring bed , no microwave , tiny fridge. The front desk was helpful but the staff working barely spoke English and weren’t very helpful. Ice machine was a floor down and when I asked they just pointed and said that way. Nice place to have a wedding but if you’re just in town for a night it is not worth the money. Paid..."Reviewed November 6, 2026Roundtrip • Orlando (MCO) - White Plains (HPN)MCO - HPN • 1 stop HPN - MCO • Nonstop$967$752found 6 hours agoper traveler - The Opus Westchester, Autograph Collection
Jan 18 - Jan 23The Opus Westchester, Autograph Collection + Flight
White Plains5 nights5.0 star property9.2/10 - Wonderful (594 reviews)"We checked in A water pipe broke No a/c No tv Hallway and hotel smelled terrible No answers when it will be fixed No manager on duty So far no compensation offered me and when I asked they said maybe they will give me 15000 miles for a 3 night stay which cost 60000 miles per night 180000 miles"Reviewed October 30, 2026Roundtrip • Orlando (MCO) - White Plains (HPN)MCO - HPN • 1 stop HPN - MCO • Nonstop
Where to stay near Darien
Stamford
Discover Stamford, a vibrant city perfect for family travelers seeking a blend of urban excitement and outdoor adventure. With attractions like the shopping hotspot Greenwich Avenue, the fascinating Glass House museum, and the charming Historic South Norwalk, there’s plenty to explore. Just about a 4-mile drive from Darien, Stamford offers a range of activities year-round, making it a smart choice for your next getaway. Enjoy the convenience and variety that Stamford has to offer for your stay!
Norwalk
Experience the charm of Norwalk, a fantastic hub for travelers seeking a blend of outdoor adventures and urban sophistication. With attractions like the historic South Norwalk, the modern Fairfield University, and the beautiful Compo Beach, there's something for everyone to enjoy. Located about 4 miles by car from Darien, Norwalk offers easy access for a weekend getaway or family vacation, making it a smart choice for your stay.
Rowayton
Make your vacation planning effortless by staying in Rowayton, a haven for leisure travelers thanks to its stunning scenery and outdoor activities. Visitors will enjoy the nearby beach and lake, perfect for family outings, as well as attractions like the historic South Norwalk and The Glass House museum. Located about 2 miles by car from Darien, Rowayton is a smart choice for those seeking a relaxing getaway with plenty to explore.
Cove - East Side - Shippan
Cove - East Side - Shippan stands out as a prime spot for family travelers interested in outdoor activities and city experiences. This vibrant neighborhood offers easy access to attractions like the beach, sports facility stadium, and urban park, making it perfect for a weekend getaway. Just about 3 miles by car from Darien, visitors can enjoy a blend of recreation and culture, including the historic charm of Greenwich Avenue and the artistic allure of The Glass House. Cove - East Side - Shippan is a smart choice for your stay, providing a delightful mix of amenities and local highlights.
Westport
Travelers visiting the area often choose Westport, especially those seeking a blend of business and leisure. With attractions like the scenic Compo Beach, the historic charm of South Norwalk, and the educational offerings at Fairfield University, Westport provides a rich experience. The city is just about a 7-mile drive from Darien, making it an easily accessible getaway. Whether you're in town for work or a weekend retreat, Westport is a smart choice for your stay.
Discover the most popular places to visit in Darien
Darien Hotel Deals
Residence Inn by Marriott Norwalk
Residence Inn by Marriott Norwalk
"Excellent"
The Lloyd Stamford, Tapestry Collection by Hilton
The Lloyd Stamford, Tapestry Collection by Hilton
"Room was so clean and bed was fabulous!! Staff is y friendly and the complimentary breakfast was outstanding!!"
"What I loved : extremely clean both in the room and the common areas , very nice and helpful staff, quiet atmosphere, comfy beds , safe parking . What was disappointing : the plumbing needs more consistent maintenance , last trip we had only hot water in the shower and had to switch rooms , this trip the bathroom sink drain had to be cleaned during our stay , and the lobby bathroom failed to flush . Also, the electric needs maintenance - three plugs did not work in my room , so I was drying my...
Frequently Asked Questions
How much does a Darien vacation package cost?
Offering excellent value package deals from $718 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.