
Darien Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Darien Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Delamar Greenwich Harbor
Price was CA $2,087, price is now CA $1,615 per person
CA $1,615
per person
Dec 24 - Dec 28
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)
Staff are very friendly. Beautiful, clean rooms. Delicious restaurant downstairs
Reviewed on Nov 8, 2026


Stamford Suites
Downtown Stamford
Price was CA $1,015, price is now CA $847 per person
CA $847
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
6.2/10 (197 reviews)
This was by far one of the worst hotel experiences I have ever had. I booked an extended stay at Stamford Suites through Orbitz and arrived to find accommodations that were filthy, deteriorating, and nothing like the advertised photos.
The suite had visible mold-like growth in the bathroom, rusted fixtures, damaged cabinetry, poorly maintained surfaces, and a leaking window that left standing water on the floor. These were not minor cosmetic issues but serious sanitation and potential health hazards.
After just one night, I developed numerous bites across my back, which I suspect were from bedbugs. I had to purchase medication and supplies to treat the irritation.
I immediately contacted Orbitz and the property, documented the conditions with photographs, and requested assistance. Instead of meaningful intervention, I encountered delays, poor communication, and little accountability. I was forced to stay one night because I had nowhere else to go. Although Orbitz eventually issued a partial refund, I was still charged an inflated first-night rate, and my Orbitz rewards were not restored.
Worst of all, I was in town following a tragic death in my family, helping prepare for a funeral. Instead of having a safe place to rest, I spent precious time dealing with unsanitary conditions, health concerns, customer service disputes, and finding alternative accommodations.
I have photographic evidence of everything. The lack of cleanliness, compassion, and accountability was insane
Reviewed on Nov 6, 2026
Darien Hotel Deals

Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Nov 11 to Nov 12
CA $281
CA $357 total
Nov 11 - Nov 12
includes taxes & fees

East Norwich Inn
6321 Northern Blvd. East Norwich NY
The price is CA $182 per night from Nov 10 to Nov 11
CA $182
CA $209 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (1,818 reviews)
"We liked that the property is very clean. The beds need to be updated. They feel old. The staff was not the friendliest. Over all we liked the price and location. We would stay again."
Reviewed on Nov 8, 2026

Sleepy Hollow Hotel, a Dolce by Wyndham
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Dec 1 to Dec 2
CA $187
CA $214 total
Dec 1 - Dec 2
includes taxes & fees
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.
Stay near popular Darien attractions
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








