Stamford Vacation Packages

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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.

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Stamford Hotel Deals

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 4 to May 5
CA $175
CA $195 total
includes taxes & fees
May 4 - May 5
8.6/10 Excellent! (999 reviews)
"Very nice and funky place! Clean, friendly nice staff. Have already stayed here twice and plan to stay again!❤️"

Reviewed on Apr. 18, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $356 per night from May 20 to May 21
CA $356
CA $398 total
includes taxes & fees
May 20 - May 21
9.6/10 Exceptional! (447 reviews)
"Wonderful staff! Welcoming, relaxed, great personalities."

Reviewed on Apr. 28, 2025

The Williams Inn
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
The price is CA $163 per night from May 8 to May 9
CA $163
CA $197 total
includes taxes & fees
May 8 - May 9
8.6/10 Excellent! (1,798 reviews)
"Great property"

Reviewed on Apr. 27, 2025

Vacation Village in the Berkshires
See all 1,423 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.

All Inclusive Vacations

All Inclusive Vacations

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Family Vacations

Family Vacations

Frequently asked questions

How much does a Stamford vacation package cost?
You’ll find cheap prices on Expedia for your Stamford escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Stamford costs.
What are the cheapest months to go to Stamford?
To pick up cheap Stamford vacation packages, organize your trip outside of peak times like public holidays and major festivals. You’ll typically find lower prices and better availability when it’s less busy.
How many days is enough for Stamford?
The ideal duration for your Stamford vacation depends on what you’d like to see. Usually, a few days to a week will give you enough time to hit all the leading sights and explore some hidden gems along the way.
How to find the best Stamford package deals?
Use Expedia’s handy filters to find some great Stamford package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or look for Stamford package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Stamford vacation as a package?
You can enjoy significant savings on your Stamford retreat by booking a customized vacation package. Check the “Package” heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Stamford?
If you’re considering an impromptu Stamford trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Stamford?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Stamford.
  2. Budget wisely: On top of the price of your hotel, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Stamford.
  3. Decide your trip length: Consider how long you’d like to spend exploring Stamford. Plan your days so you can get to all the attractions and activities you’re interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Stamford vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.