Darien Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Tim Rousseau

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
per person
Oct 13 - Oct 16
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.4/10 Very Good! (1,009 reviews)
The theme of this hotel is wellness and it's awesome. You walk in and they have ginger lime water, lemon water, and regular water to drink. The rooms are equipped with exercise bands, yoga mat and block, and a foam roller. The gym was large and well equipped and kept at a cool temperature. The lighting in the room is soft. There is an outdoor courtyard and a spacious area inside for eating and getting work done. Overall one of the best hotels I've stayed at and would highly recommend.

Reviewed on Jul. 25, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very Good! (1,008 reviews)
This has been our go to for years! A beautiful property with great dining options nearby and activities!

Reviewed on Jul. 24, 2025

Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Oct 17 - Oct 21
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to White Plains (HPN)
7.4/10 Good! (1,001 reviews)
Clean, comfortable and super quiet! Staff was very friendly and helpful

Reviewed on Jul. 15, 2025

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
Crown Heights
per person
Aug 30 - Sep 2
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.8/10 Excellent! (1,001 reviews)
My Room smelled a little sweaty. Other than that my stay was amazing.

Reviewed on Jul. 17, 2025

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (964 reviews)
I enjoyed my quick staycation at this property. It is very close to Stamford which has endless amenities. The property looks like a resort, I was very pleased to stay here. I would definitely revisit.

Reviewed on Jul. 23, 2025

Ready to book your vacation to Darien?

 

Choose your dates

Darien Hotel Deals

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $146 per night from Jul 31 to Aug 1
CA $146
CA $168 total
Jul 31 - Aug 1
includes taxes & fees
8.2/10 Very Good! (1,019 reviews)
Clean and comfortable
"I love to even Hotel I typically stay in them wherever they're available that I'm traveling to."

Reviewed on Jul. 24, 2025

EVEN Hotel Norwalk by IHG
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 24 to Aug 25
CA $202
CA $231 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,384 reviews)
"Breakfast sucks"

Reviewed on Jul. 19, 2025

Baymont by Wyndham White Plains - Elmsford
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 $187 per night from Aug 3 to Aug 4
CA $187
CA $214 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,079 reviews)
"Clean & Kindly."

Reviewed on Jul. 23, 2025

Hampton Inn White Plains/Tarrytown
See all 1,140 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
Family Vacations

Frequently asked questions

How much does a Darien vacation package cost?
You can pick up a vacation package to this destination from CA $556 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.