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.
Super 8 by Wyndham Stamford/New York City Area

Super 8 by Wyndham Stamford/New York City Area

2.5 out of 5
West Side
per person
Aug 23 - Aug 28
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to White Plains (HPN)
6.2/10 (1,003 reviews)
The Super8 was an awesome stay. Staff was polite and helpful with answering our questions...

Reviewed on Jul. 6, 2025

Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
7.4/10 Good! (1,001 reviews)
Shabby desk chair in room, wall paper in room separating at the seams, no remote control for the TV

Reviewed on Jul. 9, 2025

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Aug 28 - Sep 1
just found
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (964 reviews)
While Billy at the Bar was fantastic he had a lot to deal w and handled it well. It took almost an hour to received a salad? And then we couldn’t get the order breakfast app to work so we went to front desk to order breakfast w Alesia? very sweet but idk what happened bc after a half late we called the front desk and whoever answered went to see what happed and there was no order? So she took our order and put a rush on it

Reviewed on Jul. 12, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
per person
Aug 28 - Sep 1
just found
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very Good! (1,008 reviews)
I didnt like the hotel charged a $20 service fee... defeats the purpose of using Expedia

Reviewed on Jul. 12, 2025

Courtyard by Marriott Yonkers Westchester County

Courtyard by Marriott Yonkers Westchester County

3 out of 5
Northwest Yonkers
per person
Sep 19 - Sep 26
just found
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.8/10 Excellent! (1,200 reviews)
Check in was super quick. We actually booked a hotel across the parking lot at renaissance but their system was down so I had a book here last minute. It was so quick and easy I booked it and was in my room within five minutes. The bathroom is beautiful! The king bed was so nice I slept like a baby. I wasn’t able to use the amenities but the pool looks great! The breakfast was the best breakfast I’ve ever had! The French toast and breakfast potatoes were to die for!! I would drive 4 hours just to get the breakfast!

Reviewed on Jul. 13, 2025

Ready to book your vacation to Darien?

 

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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 $148 per night from Aug 4 to Aug 5
CA $148
CA $170 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Everything!"

Reviewed on Jul. 12, 2025

EVEN Hotel Norwalk by IHG
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 $119 per night from Jul 23 to Jul 24
CA $119
CA $138 total
Jul 23 - Jul 24
includes taxes & fees
8.4/10 Very Good! (1,610 reviews)
"Easy fjeck in and clean room. Elevator smelled ... needed a cleaning or new carpet. I would stay there again."

Reviewed on Jul. 13, 2025

Amsterdam Hotel
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 $208 per night from Aug 3 to Aug 4
CA $208
CA $238 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,376 reviews)
"Hotel is clean, modern and well maintained. Staff is friendly and responsive to any issues."

Reviewed on Jul. 9, 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,134 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

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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 $664 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.