Darien Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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.
Upscale Modern Luxury 3BR Home

Upscale Modern Luxury 3BR Home

2 out of 5
Price was CA $1,458, price is now CA $1,222 per person
CA $1,222
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
4/10 (1 review)
Property was missing needed items and it took two days to get them(coffee maker). For the price you get what you’d expect. Older property with some updates needed. Everything worked but older appliances.

Reviewed on Jan 23, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was CA $5,063, price is now CA $3,151 per person
CA $3,151
per person
Dec 28 - Jan 2
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC

2 out of 5
Bryn Mawr
Price was CA $2,873, price is now CA $2,075 per person
CA $2,075
per person
Dec 27 - Jan 3
found 13 hours ago
Roundtrip flight included
Edmonton (YEG) to White Plains (HPN)
9/10 Wonderful! (2 reviews)

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $1,862, price is now CA $1,624 per person
CA $1,624
per person
Dec 20 - Dec 24
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was CA $4,058, price is now CA $3,542 per person
CA $3,542
per person
Dec 20 - Dec 24
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) 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

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Darien Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Nov 24 to Nov 25
CA $222
CA $289 total
Nov 24 - Nov 25
includes taxes & fees
8.2/10 Very good! (1,395 reviews)
"The room was very clean!"

Reviewed on Oct 27, 2026

Tarrytown House Estate
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
The price is CA $171 per night from Nov 12 to Nov 13
CA $171
CA $196 total
Nov 12 - Nov 13
includes taxes & fees
East Norwich Inn
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
The price is CA $367 per night from Nov 21 to Nov 22
CA $367
CA $480 total
Nov 21 - Nov 22
includes taxes & fees
J House Greenwich
See all 1,203 properties in Darien
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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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.
See properties

Frequently asked questions

How much does a Darien vacation package cost?
You can pick up a vacation package to this destination from CA $1,222 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.