Weston Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Weston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
CA $1,701
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Amazing view of the city and rooftop pool is always a great time. Will be back again! Amazing staff and beautiful space.
Reviewed on Aug 17, 2026
Ready to book your vacation to Weston?
Weston Hotel Deals
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $247
CA $284 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,107 reviews)
"All good"
Reviewed on Aug 18, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $207
CA $238 total
Aug 30 - Aug 31
includes taxes & fees
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
CA $135
CA $156 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very good! (1,410 reviews)
"It's a wonderful property, just a bit dated."
Reviewed on Aug 18, 2026
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 Weston attractions
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.
Frequently asked questions
How much does a Weston vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,199 on Expedia. But how much your vacation to Weston costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Weston?
The off-season is the best time to head to Weston if you're trying to keep costs down. Another tip for getting cheap Weston vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Weston?
With about 3 days, you'll have enough time to enjoy popular neighbourhoods like Cranbury and Greenfield Hill during your Weston vacation. Be sure to also add Westport Farmers Market and Old Mill Beach to your must-do list. Searching for more adventures? Consider exploring outside of Weston on tours and day trips.
How to find the best Weston package deals?
Landing a cheap Weston package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Weston package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Weston vacation as a package?
You can enjoy significant savings on your next Weston break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Weston?
If you're considering a spur-of-the-moment Weston adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Weston?
- Pick your travel dates: What you'd like to do in Weston and your preferred season can help you decide when to get away.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and activities. Your hotel will likely be the largest expense during your trip to Weston.
- Decide how long to go away for: Now that you're up to speed on Weston, you can work out the ideal length of your vacation. Put together a rough plan and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Weston vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
