Weston Vacations from $286

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Your Weston Vacation

When you organize a vacation package to Weston, you can relax and enjoy your escape knowing that all your travel plans have been made in advance. Discover the charms of this amazing city while based in a neighborhood like Cranbury, which is great for nature. A trip to Weston is a great opportunity to do some sightseeing. Be sure to look around renowned attractions like Westport Country Playhouse, Westport Farmers Market and Silvermine Arts Center. Check out Expedia's extensive range of travel options and book your ultimate vacation to Weston now.

The Latest Weston vacation packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $564, price is now $286 per person
$286
per person
Feb 27 - Mar 2
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff was really nice, rooms were clean will definitely be staying here again

Reviewed on Jan 4, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was $2,279, price is now $1,056 per person
$1,056
per person
Mar 20 - Mar 27
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,667 reviews)
This hotel was impeccable! The helpful, friendly staff, the cleanliness of the room, the location and ease of access, and the outstanding view all made this the perfect place to experience our first time in NYC!

Reviewed on Jan 3, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $2,827, price is now $1,380 per person
$1,380
per person
Mar 20 - Mar 27
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Had a wonderful visit!

Reviewed on Dec 28, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $606, price is now $324 per person
$324
per person
Mar 18 - Mar 21
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Not the greatest rooms and had to be asked to move. New room was okay but bathroom was extremely tiny and no fridge and new room bathtub didn’t work with drain. Not the best

Reviewed on Jan 4, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $4,102, price is now $2,199 per person
$2,199
per person
Mar 20 - Mar 27
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
This hotel was FABULOUS! The view you see if the view you get! STUNNING magazine worthy view of the Brooklyn bridge. Almost kid free. The rooftop bar and lounge had stunning views of the Brooklyn bridge and Hudson river. Just minutes away from Manhattan and close enough to walk to the Bridge. Room service was excellent. Very clean room.

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in Weston

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

Weston 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 refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Jan 7 to Jan 8
$131 total
Jan 7 - Jan 8
Total with taxes and fees
8.2/10 Very Good! (1,041 reviews)
Pet friendly with really nice staff

Reviewed on Jan 2, 2026

EVEN Hotel Norwalk by IHG
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
$137 nightly
The price is $157 total per night from Jan 18 to Jan 19
$157 total
Jan 18 - Jan 19
Total with taxes and fees
7.4/10 Good! (1,013 reviews)
It was clean. Spacious and staff was awesome.

Reviewed on Jan 3, 2026

DoubleTree by Hilton Stamford
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Jan 13 to Jan 14
$121 total
Jan 13 - Jan 14
Total with taxes and fees
8.4/10 Very Good! (1,734 reviews)
This is an older affordable hotel. The room was very clean. Everything worked except the tub stopper. The staff is friendly and helpful. There is free onsite parking. A basic continental breakfast. It is convenient to the metro north station. The neighborhood is quiet and safe. Fast food and convenience ...

Reviewed on Jan 1, 2026

Amsterdam Hotel
See all 1,092 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.

Find the Best Weston Vacation Packages

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

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Frequently asked questions

How much does a Weston vacation package cost?
Offering excellent value package deals from $286 on Expedia, you'll be thrilled with how little a vacation to Weston costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Weston?
December, January and February are the best times to look for cheap Weston vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Weston?
With a well-planned schedule, you can easily tick off the main Weston attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Weston vacation for longer.
How to find the best Weston package deals?
Start your search for a Weston package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Weston package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Weston escape underway.
Is it cheaper to book a Weston vacation as a package?
You can enjoy significant savings on your next Weston getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Weston?
Enjoy amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Weston trip.
Does Expedia offer Book Now, Pay Later Weston vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Weston trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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