Stamford Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Stamford Vacation

Food, history, entertainment and more … There's a whole lot to discover with a Stamford vacation package. And with the ability to easily customize your city adventure, it's guaranteed to be one that's tough to forget. Every trip to Stamford has to include some sightseeing. What to check out first? Broad Brook Trailhead and The Dome Trailhead are leading attractions. Expedia has what you need to escape your routine. Tailor your vacation to Stamford to suit your travel style, whatever that may be.

Stamford Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Sep 28 to Sep 29
$143 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (2,013 reviews)
"Always very relaxing. Kids love the pool and we enjoy the hot tub and views"

Reviewed on Sep 21, 2025

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Oct 26 to Oct 27
$162 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
a gem
"Totally perfect for mass mocha"

Reviewed on Sep 21, 2025

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $270 total per night from Oct 27 to Oct 28
$270 total
Oct 27 - Oct 28
Total with taxes and fees
9.6/10 Exceptional! (506 reviews)
"Great hotel. Food and drinks were very good. Not much to do in the town but a great place for walking."

Reviewed on Sep 21, 2025

The Williams Inn
See all 1,438 properties in Stamford
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Stamford vacation package cost?
You'll find cheap prices on Expedia for your Stamford escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Stamford costs.
What are the cheapest months to go to Stamford?
You can usually find reduced prices and better availability in March, April and November. Explore our cheap Stamford vacation packages and you could land some excellent off-season deals.
How many days is enough for Stamford?
Generally, a handful of days is enough to visit the top attractions during your Stamford vacation. But if you prefer to have more time to unwind or take day tours, consider extending your trip.
How to find the best Stamford package deals?
Bagging a cheap Stamford package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly Stamford package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Stamford vacation as a package?
You can enjoy significant savings on your next Stamford retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat 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 Stamford?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Stamford adventure.
Does Expedia offer Book Now, Pay Later Stamford vacation packages?
If you're like us, you love exploring new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Stamford trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.