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.
Modern Comfort in the Heart of NYC
Southeast Yonkers
CA $1,037
per person
Oct 29 - Nov 2
found 9 hours ago
Roundtrip flight included
Toronto (YTO) 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 NY Home with Free Parking
CA $5,269
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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
3BR Prime Luxury NY - Free Parking
CA $4,383
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
6/10 (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 on Mar 30, 2026
Luxury NYC Home Game Room Free Parking
CA $2,773
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
4/10 (1 review)
After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is that there was a plumbing problem and they would get us to another property from the original property manager and Expedia NOT doing a thing to help 4 of us stranded with no place to stay, we got to the other property. The new property was fine, but the most upsatting thing was dealing with Expedia trying to get a place for us to stay. Expedia tried saying they would cancel the accommodations and get us a Hotel but we would have to pay for the hotel and then wait for any credits or refund on our original booking. HIGHLY unacceptable by Expedia customer service. I am a GOLD member and spend quite a few thousand dollars a year for both business and pleasure and they did NOTHING to make me feel they were taking care of us. We basically lost a day of full work which cost my business over $1500 in non productive work.
Reviewed on May 4, 2026
Ready to book your vacation to Darien?
Darien Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $226
CA $293 total
Oct 1 - Oct 2
includes taxes & fees
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
CA $157
CA $179 total
Sep 20 - Sep 21
includes taxes & fees
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $237
CA $317 total
Sep 27 - Sep 28
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
Woodland Park
After visiting Woodland Park, make a plan to see the other sights and activities in Darien. Wander the parks and beaches while you're in the area.
McGuane Field
After visiting McGuane Field, make a plan to see the other sights and activities in Darien. Check out the shops and top-notch restaurants in this romantic area.
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
You can spend an afternoon browsing the exhibits at The Mather Homestead during your travels in Darien. Amble around the area's parks or visit its shops.
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.
David Fetter Park
David Fetter Park is just one of the places to see in Darien, so why not enjoy the other things to explore during your travels? Wander the parks and beaches while you're in the area.
Frequently asked questions
How much does a Darien vacation package cost?
You can pick up a vacation package to this destination from CA $1,037 on Expedia. However, how much your vacation to Darien costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Darien?
Plan your getaway for the low or shoulder season and you're likely to score cheap Darien vacation packages. Bear in mind that public holidays and major festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Darien?
Darien vacations can be short or long, but to really sink your teeth into this place, we'd say 4 days is about right. This will mean you can visit major attractions like The Glass House and The Maritime Aquarium along with underrated spots. Don't forget to explore neighbourhoods such as Downtown Stamford and Cove - East Side - Shippan either. If you're clever with your time, you can even allow for a day trip from Darien too.
Is it worth booking a vacation package to Darien?
Darien has everything you need for an awesome getaway — views, coastal beaches and golfing are just the start. Whether you want to visit attractions like Sleepy Hollow Park and Sapelo Island Visitors Centre, or take the path less travelled, you'll find plenty to do on your Darien vacation.
How to find the best Darien package deals?
Begin your search for a Darien package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Darien package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Darien adventure underway.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Darien vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Darien?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Darien break.
How to plan a trip to Darien?
- Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Darien.
- Plan your budget wisely: On top of the cost of your hotel, you should factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Darien.
- Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Darien. Then, estimate how long you'll need at each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Darien vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
