Stamford Vacation Packages
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Your Stamford Vacation
The cosmopolitan vibe, rich history and coastal scenery are just some of the reasons why people fall in love with this beachy city. Discover this vibrant destination in whatever way you choose with a Stamford vacation package. You'll want to take in the sights during your trip to Stamford. Find time for popular attractions like Chelsea Piers, The Glass House and Greenwich Avenue. Browse Expedia's wide range of travel options and book your ideal vacation to Stamford today.
Top Stamford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Luxury 1BR located in Prime Yonkers Area
Bryn Mawr
CA $1,327
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
4.8/10 (6 reviews)
C completely misrepresented did not stay there far from a luxury apartment advised to check into a different location no code or communication prior to check in time at 4 PM. Received emails and poor communication after 6:30 PM apartment smelled very musty and like a dead body was inside, extremely unprofessional and horrible experience.
Reviewed on May 5, 2026
Modern Comfort in the Heart of NYC
Southeast Yonkers
CA $1,411
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Where to stay in Stamford
Find the best Stamford areas and neighborhoods for the activities you enjoy most. Learn more about Stamford
Downtown Stamford
2 out of top 10 points of interest in this area
Central business district with major retail establishments, a shopping mall, and a university campus. Explore the historic district's architecture, enjoy bars and restaurants near Columbus Park, and easily access the Metro-North train station.
Cove - East Side - Shippan
2 out of top 10 points of interest in this area
While visiting Cove - East Side - Shippan, you might make a stop by sights like West Beach and Chelsea Piers.
South End
While South End might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Stamford Town Center and Stamford Center for the Arts.
Waterside
While there might not be top attractions in Waterside, you can explore the larger area and discover places like Stamford Town Center and Stamford Center for the Arts.
West Side
1 out of top 10 points of interest in this area
While there might not be top attractions in West Side, you can explore the larger area and discover places like Stamford Center for the Arts and E. Gaynor Brennan Golf Course.
Ready to book your vacation to Stamford?
Stamford Hotel Deals
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
CA $137
CA $159 total
Oct 24 - Oct 25
includes taxes & fees
8.4/10 Very good! (1,780 reviews)
"My stay will make me look forward to next"
Reviewed on Sep 23, 2026
La Quinta Inn & Suites by Wyndham Stamford / New York City
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
CA $134
CA $154 total
Oct 18 - Oct 19
includes taxes & fees
6.6/10 (1,741 reviews)
"It’s being renovated. The night girl was a real B word"
Reviewed on Sep 23, 2026
The Stamford Hotel
700 East Main Street Stamford CT
Fully refundableReserve now, pay when you stay
CA $237
CA $273 total
Oct 1 - Oct 2
includes taxes & fees
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 Stamford attractions
Stamford Town Center
8.6/10 (374 reviews)
You can find the perfect gifts to bring home at Stamford Town Center during your trip to Stamford. Check out the top-notch restaurants or lively bars in this family-friendly area.
Cove Island Park
8.0/10 (31 reviews)
If a restful vacation is part of your travel plans, Cove Island Park might be the perfect place to seek out during your trip to Stamford. Check out the shops and top-notch restaurants in this family-friendly area.
Chelsea Piers
8.0/10 (271 reviews)
Take the family on an outing to Chelsea Piers during your trip to Stamford. Savor the lively bars and top-notch restaurants while in town.
Stamford Center for the Arts
7.8/10 (127 reviews)
Enjoy a performance at Stamford Center for the Arts, a storied theater in Stamford. Check out the lively bars or top-notch restaurants in this family-friendly area.
Stamford Museum and Nature Center
8.2/10 (113 reviews)
You can spend an afternoon studying the exhibits at Stamford Museum and Nature Center in Stamford. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
West Beach
7.6/10 (37 reviews)
Why not spend a lazy afternoon at West Beach during your trip to Stamford?
Hand & Stone Massage and Facial Spa
7.8/10 (32 reviews)
You can take time to visit Hand & Stone Massage and Facial Spa during your travels to Stamford. Check out the lively bars or top-notch restaurants in this family-friendly area.
Curtain Call
8.0/10 (70 reviews)
You can get tickets for a performance at Curtain Call on your trip to Stamford. Discover the lively bars and entertainment choices in this family-friendly area.
What to do in Stamford
Introductory Helicopter Flight Lesson from Westchester
CA $975
per traveller
Frequently asked questions
How much does a Stamford vacation package cost?
Offering great value package deals from CA $1,327 on Expedia, you'll be thrilled with how little a vacation to Stamford costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stamford?
You can usually find reduced prices and greater availability in January, February and April. Explore our cheap Stamford vacation packages and you could get some great off-season discounts.
How many days is enough for Stamford?
With about 2 days, you'll have enough time to experience popular neighbourhoods such as Downtown Stamford and Cove - East Side - Shippan during your Stamford vacation. Remember to also add The Glass House and Greenwich Point Park to your sightseeing itinerary. Up for some more adventures? Consider exploring outside of Stamford on day trips and tours.
Is it worth booking a vacation package to Stamford?
It's no wonder a Stamford vacation is on the must-do list of many travellers. Well-known attractions like Chelsea Piers are just the start of what you can explore here.
How to find the best Stamford package deals?
Use Expedia's handy filters to help you find some tempting 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 want to save, plan your break for midweek, or search for Stamford package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Stamford vacation as a package?
You can enjoy significant savings on your next Stamford break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save 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've got your Stamford vacation dates confirmed, book early to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Stamford?
- Pick your travel dates: What you plan to do in Stamford and your favourite season can help you decide when to get away.
- Budget wisely: As well as the price of your accommodations, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Stamford.
- Work out your trip length: Think about how long you want to spend discovering Stamford. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, book the perfect Stamford vacation package for you.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
