Weston Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Weston Vacation Packages

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 SARĀ 796 per night from Aug 4 to Aug 5
SARĀ 796
SARĀ 916 total
4 Aug - 5 Aug
includes taxes & fees
Hyatt Regency Greenwich
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
The price is SARĀ 402 per night from Aug 2 to Aug 3
SARĀ 402
SARĀ 463 total
2 Aug - 3 Aug
includes taxes & fees
6.6/10 (1,546 reviews)
"The property is being renovated, however it is above average. The Staff is very helpful and most importantly the room was clean"

Reviewed on 16 July 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
The price is SARĀ 560 per night from Jul 19 to Jul 20
SARĀ 560
SARĀ 643 total
19 Jul - 20 Jul
includes taxes & fees
Trumbull Marriott Shelton
See all 1,114 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.

Stay near popular Weston attractions

Lucius Pond Ordway / Devil's Den Preserve

Connecticut's largest preserve offers 20 miles of trails through diverse woodlands, wetlands, and rocky ridges. Explore Devil's Den's tranquil landscape where birds and wildlife like bobcats and red foxes thrive.
See properties

Frequently asked questions

How much does a Weston vacation package cost?
You can pick up a vacation package to this popular destination 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 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.