Weston Vacations from $223

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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 $454, price is now $223 per person
$223
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (2,008 reviews)
Had a very nice view. Hotel very central and calm

Reviewed on Nov 19, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $647, price is now $318 per person
$318
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
I’m honestly tempted to gatekeep this place because it’s such a gem. I was pleasantly surprised by how much I enjoyed my stay. The room was clean, spacious by NYC standards, and had a nice mid-to-modern vibe. The staff was great — attentive, kind, and fast. I requested room service and it happened quickly, and when I realized I was missing something from the room, they brought it right up with no issues. The on-property restaurant was amazing (truly delicious), and the front-of-house team was warm and on point the whole time. Overall, I don’t have a single complaint. they are doing an incredible job with customer service. Kudos to the entire team.

Reviewed on Nov 19, 2025

Kimpton Theta New York - Times Square by IHG

Kimpton Theta New York - Times Square by IHG

4 out of 5
Manhattan
Save 100% on your flight
Price was $777, price is now $400 per person
$400
per person
Jan 22 - Jan 27
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.6/10 Exceptional! (1,265 reviews)
Room was fine. The wall decor was a bit strange and the bed was pretty hard. The staff was decently pleasant and helpful and the blow dryer was way better than the small ones some hotels leave ya. No major complaints.

Reviewed on Nov 19, 2025

Holiday Inn Express & Suites Woodside LaGuardia Airport by IHG

Holiday Inn Express & Suites Woodside LaGuardia Airport by IHG

2.5 out of 5
Queens
Save 100% on your flight
Price was $432, price is now $225 per person
$225
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18/10 Exceptional! (1,123 reviews)
Shuttle available only for LaGuardia airport.

Reviewed on Nov 16, 2025

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,556, price is now $818 per person
$818
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
19.2/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 2025

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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

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $178 total per night from Dec 21 to Dec 22
$178 total
Dec 21 - Dec 22
Total with taxes and fees
7.4/10 Good! (1,009 reviews)
The room was clean and safe. The staff were friendly and the Hilton signature cookie was delicious. My one criticism is the place could use a little TLC. The faux leather on the chair is my room was cracked and peeling, the print hanging on the wall had slipped out of its matting and was crooked ...

Reviewed on Nov 8, 2025

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
$103 nightly
The price is $119 total per night from Nov 22 to Nov 23
$119 total
Nov 22 - Nov 23
Total with taxes and fees
8.4/10 Very Good! (1,719 reviews)
I wish I could give four and a half stars. The front desk staff is excellent — friendly and helpful. We were prepared for the dated look of the hotel thanks to the accurate Expedia reviews. And we weren’t disappointed in the cleanliness of the property, which is one of the main reasons we chose this ...

Reviewed on Nov 16, 2025

Amsterdam Hotel
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue Norwalk CT
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $131 total per night from Nov 30 to Dec 1
$131 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,367 reviews)
Amazing! Renovations are awesome. Pool was gorgeous and food is excellent. They have a new chef, new menu and pool side bar. Very accommodating. We live in the area and came here as a staycation with the pool the last week of summer. Staff is lovely and grounds are lovely as well. Maria the owner ...

Reviewed on Nov 15, 2025

Norwalk Inn & Conference Center
See all 1,082 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 $223 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.