Darien Vacation Packages

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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.
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Price was CA $1,150, price is now CA $880 per person
CA $880
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very Good! (1,003 reviews)
What a Gem. The room spacious and clean ( tub definitely needs elbow grease but that’s why shower shoes are a thing). Overall, The entire team was amazing. It’s a resort like feeling North of Manhattan. THE FOOD OMG where to begin nothing let me down over the four nights!!!! Dominique, Nicole, and Teddy-and the locals who frequent are the reasons we will come back - NOMA SOCIAL just continue to play a variety of music becasue although I love my latin music it was overkill and DJ’s must represent rhe NYC culture to entirely with a good mix and not a centered focus on one genre- BUT STILL A FAVORITE PLACE!!

Reviewed on Aug. 20, 2025

Dome House Retreat

Dome House Retreat

4 out of 5
Price was CA $3,567, price is now CA $2,483 per person
CA $2,483
per person
Sep 26 - Oct 1
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
No reviews
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Price was CA $3,836, price is now CA $2,730 per person
CA $2,730
per person
Oct 9 - Oct 13
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was CA $1,283, price is now CA $988 per person
CA $988
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
7.8/10 Good! (1,123 reviews)
Quiet friendly clean

Reviewed on Aug. 21, 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Price was CA $4,102, price is now CA $3,168 per person
CA $3,168
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
2/10 (1 review)

Ready to book your vacation to Darien?

 

Choose your dates

Darien Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 1 to Sep 2
CA $176
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,126 reviews)
"Pool not in service. Concrete around pool and walk to parking lot in poor shape. Excellent breakfast and well staffed"

Reviewed on Aug. 19, 2025

Hampton Inn White Plains/Tarrytown
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 24 to Aug 25
CA $161
CA $186 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,283 reviews)
"This hotel has great food, drink and meeting spaces My room was extremely comfortable and clean. Would highly recommend for business and leisure activities A+"

Reviewed on Aug. 21, 2025

Norwalk Inn & Conference Center
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Sep 8 to Sep 9
CA $115
CA $134 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very Good! (1,637 reviews)
"Good deal for the price. Room clean, staff always pleasant, professional and helpful"

Reviewed on Aug. 19, 2025

Amsterdam Hotel
See all 1,133 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.
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Frequently asked questions

How much does a Darien vacation package cost?
You can pick up a vacation package to this destination from CA $880 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.