Stamford Vacations

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    Save up to ￥45,448 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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Find the Best Stamford Vacation Packages

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
8.6/10 Excellent! (1,860 reviews)
"Activities look good during week but we miss them on our weekend stay"

Reviewed on Jul 8, 2025

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Vacation Village in the Berkshires
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 ￥35,022 per night from Aug 10 to Aug 11
￥35,022
￥39,119 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (463 reviews)
"The Williams Inn is very close to Williams college and the Clark museum, both in walking distance. Very good food and services. The place is new or remodeled. Water and coffee available at each floor. I like the decor a lot. One thing that I didn't give a 5 stars is that the room clean service didn't ..."

Reviewed on Jul 8, 2025

The Williams Inn
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 ￥21,006 per night from Aug 10 to Aug 11
￥21,006
￥23,465 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (999 reviews)
Pleasant
"Spacious room with a great view, only complaint would be the gaps in the door that let noise and light in and out."

Reviewed on Jul 8, 2025

Hotel Downstreet, Ascend Hotel Collection
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.

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?
Plan your trip for the low or shoulder season and you're likely to get cheap Stamford vacation packages. Bear in mind that school vacation periods and major events and festivals can have an impact on prices, so do some research before you go.
How many days is enough for Stamford?
Typically, a handful of days is enough to tick off the main attractions during your Stamford vacation. But if you prefer to have more time to relax 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.
How to plan a trip to Stamford?

  1. Choose your travel dates: The things you want to do in Stamford and your favorite season can help you decide when to get away.
  2. Set your budget: Consider costs like flights, food and transportation when working out how much to set aside for your trip to Stamford. Then, pick a hotel that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Decide how many days away: Start by making a list of all the activities and sights you want to experience in Stamford. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Stamford vacation package that brings all your bookings together.

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