Deals on vacations and trips to Darien

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Darien flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Delamar Westport

Delamar Westport

4 out of 5
Price was $1,038, price is now $826 per person
$826
per person
Oct 3 - Oct 7
found 23 hours ago
Roundtrip non-stop flight included
Evansville (EVV) to White Plains (HPN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and free perks like buffet breakfast and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.
Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

4 out of 5
Save 100% on your flight
Price was $1,495, price is now $1,071 per person
$1,071
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, dry cleaning, and laundry facilities are also on offer.
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

4 out of 5
Save 100% on your flight
Price was $1,245, price is now $907 per person
$907
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. A garden, laundry facilities, and a virtual front desk are also on offer.
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,547, price is now $1,991 per person
$1,991
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to White Plains (HPN)
A rooftop terrace, free self parking, and laundry facilities are featured at this vacation home. Dry cleaning is also provided.
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was $3,279, price is now $2,576 per person
$2,576
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the onsite laundry facilities and in-room childcare. Dry cleaning and luggage storage are also provided.

Top Darien hotels deals

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Free Cancellation
Reserve now, pay when you stay
$201 nightly
The price is $230 total per night
$230 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $129 total per night
$129 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-in and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $232 total per night
$232 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the 24-hour gym and perks like free airport pick-up.
Pool
Free airport shuttle
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
$179 nightly
The price is $206 total per night
$206 total
Sep 27 - Sep 28
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.
Pool
Pet friendly
Westchester Marriott

Westchester Marriott

4.5 out of 5
670 White Plains Rd Tarrytown NY
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $213 total per night
$213 total
Sep 6 - Sep 7
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Spa
Parking included
Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike Westbury NY
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $93 total per night
$93 total
Sep 16 - Sep 17
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
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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.

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 are vacation packages to Darien?
Travelocity provides package deals to Darien, as well as flights and hotels, starting at just $826. With the cash you save, you could book some popular tours or even add on a few extra nights to your vacation.
Where can I get the best vacation package deals for Darien?
With at least 400 airline partners and 1,000,000 properties all over the world, it's hard to top Travelocity. Look through our extensive range and grab an affordable Darien vacation package. Don't you just love it when traveling is that easy?
Why should I book my Darien vacation bundle with Travelocity?
Because we believe in creating stress-free travel experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our support team is on hand 24/7 to make sure you're never alone. We also have a Price Match Guarantee, so you can secure your getaway knowing you've landed the best deal around. If you find a lower price, we'll match it!
Can I save on my Darien car rental if I combine it with hotels and flights?
Certainly — bundle your car, flight and hotel into a Darien vacation package and you can save a tidy sum. With so many things to do in Darien, that set of wheels will make exploring easy. Once you're in the driver's seat, crank up the music and make your way to Times Square, a must-see sight around 35 mi from Darien.
Which airport is best for Darien?
John F. Kennedy Intl. Airport (JFK) is one of the best airports for Darien. It's situated 35 mi southwest of the bustling downtown area. Your other choices are Liberty Intl. Airport (EWR) (45 mi away from central Darien) and LaGuardia Airport (LGA) (30 mi away from central Darien).
What is there to do in Darien?
Sleepy Hollow Park is one of the superb sights that make Darien a popular place to visit. But give yourself enough time to explore its lesser-known attractions too. This is sometimes where the best memories are made.
Where should I stay when visiting Darien?
Many people opt to hit the hay at the Beautiful 5 bedroom Darien house with pool. It's sure to be a great base for your Darien getaway.

Photos of local treasures

Browse Darien vacation photos for more inspiration

Two wooden benches facing a calm body of water under a clear sky.
A calm harbor with boats, a pier, and houses along the shoreline.
A sailboat on calm water with a clear sky.