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.
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
Waterside
Price was CA $910, price is now CA $775 per person
CA $775
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.6/10 (1,493 reviews)
This morning there was no water for the shower in the bathroom. No water hot or cold at all. We had to leave for the airport so we left without shower or shaving. It will be a long time before we come back here again.

Reviewed on Jul 9, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $1,892, price is now CA $1,417 per person
CA $1,417
per person
Aug 22 - Aug 25
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (992 reviews)
Valet parking is a good feature - but it was to find a valet. Had to find our own car twice. Again a welcome chocolate bar is nice, but really 1 small bar for 2 large adults. At $600 a night , I think you can spring for 2.

Reviewed on Jul 7, 2026

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Price was CA $1,382, price is now CA $1,099 per person
CA $1,099
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.6/10 Excellent! (1,161 reviews)
Stayed here for a one-night trip to Nyack. Served all our needs for location, comfort, cleanliness, and available amenities.

Reviewed on Jul 10, 2026

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was CA $1,476, price is now CA $1,182 per person
CA $1,182
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.2/10 Very good! (1,131 reviews)
The room was perfect. There is a nice gym. Coffee always available in the lobby

Reviewed on Jul 10, 2026

Hyatus Luxury Residences Stamford

Hyatus Luxury Residences Stamford

4.5 out of 5
Downtown Stamford
Price was CA $1,701, price is now CA $1,378 per person
CA $1,378
per person
Aug 22 - Aug 25
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.8/10 Exceptional! (25 reviews)
great location, with garage spaced ( thought that is a bit confusing to figure out where the space was located); apartment was super comfy, nice size and layout, with living room/open kitchen concept (complete with all cooking and utensils ). Large bathroom w/a nice shower. Towels were wet but we worked that part out. great gym facilities in building and a fun basement equipped with (adult) games! rooftop was not open, even to enjoy the sunny day.. which meant the pool too was not available. I will definitely stay here agin

Reviewed on May 3, 2026

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Darien Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
The price is CA $170 per night from Jul 30 to Jul 31
CA $170
CA $194 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very good! (1,544 reviews)
"Avoid at all costs! Price was great, but now I know why. Not sure if maintenance has EVER been done at this property and the room MIGHT have been cleaned at some point in the last few months."

Reviewed on Jul 9, 2026

Hampton Inn White Plains/Tarrytown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
The price is CA $259 per night from Aug 9 to Aug 10
CA $259
CA $298 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,074 reviews)
"Very Beautiful Hotel Excellent check in & service provided at Front Office by Soile"

Reviewed on Jul 10, 2026

Hyatt Regency Greenwich
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
The price is CA $236 per night from Aug 9 to Aug 10
CA $236
CA $316 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,326 reviews)
"I enjoyed my stay down to the pool but is far from the main museums"

Reviewed on Jul 9, 2026

Sonesta White Plains Downtown
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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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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.
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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 $775 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.