Weston Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Weston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 reviews)
Clean and room big enough. No microwave and refrigerator

Reviewed on Oct 28, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was CA $5,063, price is now CA $3,151 per person
CA $3,151
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (713 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $4,919, price is now CA $3,202 per person
CA $3,202
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,370, price is now CA $1,545 per person
CA $1,545
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

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Weston Hotel Deals

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Nov 19 to Nov 20
CA $275
CA $317 total
Nov 19 - Nov 20
includes taxes & fees
8.8/10 Excellent! (1,193 reviews)
"I will definitely be back. such a great hotel. Especially love the lobby and staff; the rooms are super cute and cozy."

Reviewed on Oct 27, 2026

Hyatt Regency Greenwich
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
The price is CA $367 per night from Nov 20 to Nov 21
CA $367
CA $481 total
Nov 20 - Nov 21
includes taxes & fees
J House Greenwich
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
2701 Summer St Stamford CT
The price is CA $238 per night from Nov 1 to Nov 2
CA $238
CA $274 total
Nov 1 - Nov 2
includes taxes & fees
7.8/10 Good! (983 reviews)
"Room very clean & spacious, friendly staff. The parking garage was a huge bonus… really enjoyed my stay here"

Reviewed on Oct 28, 2026

The Armon Stamford Hotel & Conference
See all 1,127 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
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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.
See properties

Frequently asked questions

How much does a Weston vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,017 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?

  1. Pick your travel dates: What you'd like to do in Weston and your preferred season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.