Weston Vacations from $503

Book a Hotel + Flight or Car together to unlock savings

Looking for sports, concerts, or music festivals? Opens in a new windowSearch event tickets

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 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 Weston Vacation

With every last detail organized before you take off, our Weston vacation packages mean you can concentrate on letting the good times roll. Whether you base yourself in the neighborhood of Cranbury, which is great for nature, or another area, this fun city offers a wealth of discoveries. Make your trip to Weston even more fun and exciting by going sightseeing. Levitt Pavilion, Westport Country Playhouse and Wilton Historical Society are some of the top attractions worth exploring. Your ultimate Weston vacation is just clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

The Latest Weston Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (3,679 reviews)
I asked the front desk for ice at 10:30pm. They told me it was too late and that I needed to go to the bar to get some. Later I found out that there was an ice machine in the lounge in my floor (26th)! I notified the front desk that I had trouble charging my devices because there was only one available outlet in the room. There was an USB outlet by the bed, but it was controlled by the light switch, so when I shut the light, it stopped charging. I told them to send someone to take a look the next day while we were out. When we got to the room at 11pm,a technician was already working on it, so we could not go to sleep! He was not able to fix it. The next day it seemed like someone came to fix it. It worked for a little while only...

Reviewed on Jun 5, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (547 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
This place is perfect

Reviewed on Jun 4, 2024

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
Great location! Great service!

Reviewed on May 20, 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,011 reviews)
Great for biz travelers!

Reviewed on Jun 5, 2024

Weston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

Weston Hotel Deals

Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is $100 per night from Jun 9 to Jun 10
$100
$116 total
includes taxes & fees
Jun 9 - Jun 10
8.4/10 Very Good! (1,514 reviews)
"Good value. Very clean. Very nice staff. The room is outdated. Beds were too soft not too comfortable. AC worked well but was loud when it kicked on. I would definitely recommend this property if you need a clean , friendly place to stay for a good price."

Reviewed on Jun 3, 2024

Amsterdam Hotel
The Circle Hotel Fairfield
The Circle Hotel Fairfield
3 out of 5
417 Post Road, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is $129 per night from Jun 30 to Jul 1
$129
$148 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,127 reviews)
"We were in town for one night to visit family. The location was convenient with casual dining options nearby. We enjoyed our room facing the pool! Beds were comfortable. Shower pressure was excellent. Rooms are large with pleasant nautical decor."

Reviewed on Jun 4, 2024

The Circle Hotel Fairfield
La Quinta Inn & Suites by Wyndham Stamford / New York City
La Quinta Inn & Suites by Wyndham Stamford / New York City
2.5 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is $79 per night from Jun 16 to Jun 17
$79
$91 total
includes taxes & fees
Jun 16 - Jun 17
5.6/10 (1,085 reviews)
"Nice. Reliable. Clean. Hospitality. Good"

Reviewed on Jun 2, 2024

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 988 properties in Weston
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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Weston vacation package cost?
Perhaps less than you imagined — from a low $503, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made travel package, your trip to Weston is only clicks away.
How do I get a cheap travel package to Weston?
Find flights that fit in with your schedule, add a hotel to your booking and watch the savings pile up with a Weston vacation package. It’s as simple as that! From hotels and flights to tours and rental cars, Expedia is your gateway to cheap travel. And with more than 550 partner airlines and 1,000,000 hotels across the globe to select from, you won’t be short of choice.
Where should I stay in Weston?
An escape to Weston isn’t complete without paying a visit to Wilton Historical Society. Why not choose a hotel close to this interesting attraction?
What are the top hotels in Weston?
Whether you’re staying for one night or a week in Weston, you’ll get a good night’s rest at A Private Room For Any Traveler. This place is a favorite with many travelers.
How far in advance should I book my Weston vacation?
To score discount prices, book early. Airlines usually advertise flights, along with some of the lowest fares, around a year in advance. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you’re in need of a last-minute getaway in Weston, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Weston travel package include?
From hotels and flights to car rentals, Expedia can help you shape a Weston package that’s right for you. Vacationing for a week or two? Give some thought to a rental car, flight and hotel bundle. If you can only manage a quick getaway, a hotel and airfare deal may be more your style. Experiences can also be added once you’ve made your booking. Our packages make it easy to plan and save.
What should I know before booking a Weston travel package?
Bundling your bookings into a Weston vacation package is the easiest way to organize your trip. Not only that, you’ll get great discounts when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Weston Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Just choose the carrier that suits you and craft your ideal Weston getaway.
If I'm not able to travel, can I cancel my Weston vacation package?
Whether it’s your flight or hotel, yes, you can cancel or amend it. Booked your Weston vacation package in the last 24 hours? You may be able to make any changes for free. If it’s been longer than that, you may be charged a fee by your hotel, airline or car rental company. For more information, head to our Customer Service Portal. We’re here to help you every step of the way.

Discover the most popular places to visit in Weston

Image for Lucius Pond Ordway / Devil's Den Preserve

Lucius Pond Ordway / Devil's Den Preserve

Explore the great outdoors at Lucius Pond Ordway / Devil's Den Preserve, a lovely green space in Weston. While you're here, you can savor the top-notch restaurants.

Lucius Pond Ordway / Devil's Den Preserve

Other vacations you might like

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