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*
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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.
Top Darien Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Delamar Southport
CA $1,318
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.6/10 Exceptional! (510 reviews)
Loved it! Staff very friendly and helpful, epic breakfast and fun bar scene downstairs.
I feel it’s overpriced or I would have gone with 5 stars.
Reviewed on Sep 15, 2026
Ready to book your vacation to Darien?
Darien Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
CA $219
CA $302 total
Sep 27 - Sep 28
includes taxes & fees
Inn at Jericho
101 Jericho Turnpike Westbury NY
Fully refundableReserve now, pay when you stay
CA $124
CA $139 total
Oct 12 - Oct 13
includes taxes & fees
Westchester Marriott
670 White Plains Rd Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $274
CA $314 total
Oct 18 - Oct 19
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Darien vacation package cost?
You can pick up a vacation package to this destination from CA $763 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.
