Stamford Vacations
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Where to stay in Stamford
Find the best Stamford areas and neighborhoods for the activities you enjoy most. Learn more about Stamford
Downtown Stamford
3 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
3 out of top 10 points of interest in this area
While visiting Cove - East Side - Shippan, you might make a stop by sights like Cummings Park Beach and West Beach.
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.
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.
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.
Find the Best Stamford Vacation Packages
Stamford Hotel Deals
La Quinta Inn & Suites by Wyndham Stamford / New York City
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
₩136,368
₩156,823 total
Sep 7 - Sep 8
includes taxes & fees
6.6/10 (1,642 reviews)
"The room was clean, getting checked in by the snippy staff wasn’t quite the experience I thought it would be. While waiting quite a long time to get checked in because no one was at the front desk, and no way to contact any one, we looked up google reviews and saw some rather bad ones. Thinking there’s ..."
Reviewed on Aug 12, 2026
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
₩144,544
₩167,529 total
Aug 31 - Sep 1
includes taxes & fees
Red Carpet Inn
1209 E Main St Stamford CT
Fully refundableReserve now, pay when you stay
₩127,525
₩146,656 total
Aug 16 - Aug 17
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)
Stamford Town Center offers nearly 100 retailers anchored by Macy's and Connecticut's largest Barnes & Noble. Explore the diverse shopping options, then unwind at one of the Plaza's distinctive dining establishments.
Cove Island Park
8.0/10 (31 reviews)
This coastal sanctuary along Long Island Sound features two sandy beaches and a wildlife haven with 309 bird species. Stroll the one-mile loop trail or explore the Wildlife Sanctuary for exceptional birdwatching.
Chelsea Piers
8.0/10 (271 reviews)
This 400,000-square-foot sports complex offers ice skating, swimming, gymnastics, tennis, and more under one roof. Visit weekday mornings for a less crowded experience with state-of-the-art facilities.
Stamford Center for the Arts
7.8/10 (127 reviews)
This historic venue showcases diverse performances in an intimate 1,580-seat theater with superb acoustics. Experience Broadway shows, concerts, and cultural events in Stamford's premier arts destination.
West Beach
7.6/10 (37 reviews)
This 26-acre shoreline along Long Island Sound offers clean sand and picturesque coastal views. Enjoy swimming, beach volleyball, or simply unwind at one of the picnic areas while watching the sunset over the water.
Cummings Park Beach
6.4/10 (5 reviews)
Cummings Park offers 79 acres of beachfront escape with a scenic boardwalk along Long Island Sound. Enjoy the sandy shore, fishing pier, and sports courts while taking in refreshing coastal breezes.
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.
Frequently asked questions
How much does a Stamford vacation package cost?
You'll find cheap prices on Expedia for your Stamford break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Stamford costs.
What are the cheapest months to go to Stamford?
If you're looking to snag a cheap Stamford vacation package, consider visiting in January, February and April. You're likely to find better prices on flights and hotels during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Stamford?
We suggest planning a Stamford vacation for a minimum of 2 days. This will allow you enough time to check off key attractions such as Cummings Park and Curtain Call, and check out neighborhoods like Downtown Stamford and Cove - East Side - Shippan. You could even squeeze in a day trip (or two) beyond Stamford.
Is it worth booking a vacation package to Stamford?
Stamford is a good vacation destination with attractions like Chelsea Piers among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Stamford vacation promises fun for everyone.
How to find the best Stamford package deals?
Use Expedia's filter tool to help you find some terrific Stamford package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Stamford package deals in the off-peak season. Play around with 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 soon as possible.
Is it cheaper to book a Stamford vacation as a package?
You can enjoy significant savings on your Stamford getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Stamford?
If you've got your Stamford travel dates locked in, book as early as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Stamford?
- Pick your travel dates: What you want to do in Stamford and your favorite season can help you decide when to go.
- Plan your budget wisely: In addition to the price of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Stamford.
- Decide how long to go away for: Now that you're up to speed on Stamford, you can work out the perfect length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
- Bundle your hotel and flights: 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.
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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.
