A cityscape with a river, modern buildings, and green spaces.

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.
  • An outdoor seating area with modern furniture, a fire pit, and ambient lighting.
    Dec 11 - Dec 14

    Sonesta White Plains Downtown + Flight

    White Plains
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,355 reviews)
    Roundtrip • Toronto (YTO) - White Plains (HPN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $927
    CA $796
    per traveller
    found 1 day ago
    Sonesta White Plains Downtown
  • The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.
    Dec 11 - Dec 14

    Stamford Suites + Flight

    Downtown Stamford
    3 nights
    4.0 star property
    6.2/10 - (208 reviews)
    "This was by far one of the worst hotel experiences I have ever had. I booked an extended stay at Stamford Suites through Orbitz and arrived to find accommodations that were filthy, deteriorating, and nothing like the advertised photos. The suite had visible mold-like growth in the bathroom, rusted fixtures, damaged cabinetry, poorly maintained surfaces, and a leaking window that left standing water on the floor. These were not minor cosmetic issues but serious sanitation and potential health..."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - White Plains (HPN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,009
    CA $842
    per traveller
    found 1 day ago
    Stamford Suites
  • A garden with stone steps leading to a stone structure, surrounded by lush greenery and flowering plants.
    Dec 12 - Dec 16

    Stanton House Inn + Flight

    Greenwich
    4 nights
    3.5 star property
    9.6/10 - Exceptional (186 reviews)
    Roundtrip • Toronto (YTO) - White Plains (HPN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,489
    CA $1,261
    per traveller
    found 1 day ago
    Stanton House Inn
  • A restaurant with outdoor seating, a white facade, and a sign reading "ARTISAN".
    Dec 11 - Dec 14

    Delamar Southport + Flight

    Southport
    3 nights
    4.0 star property
    9.6/10 - Exceptional (528 reviews)
    "No complaints great location and clean"
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - White Plains (HPN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,277
    CA $1,088
    per traveller
    found 1 day ago
    Delamar Southport
  • An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.
    Dec 11 - Dec 14

    Westchester Marriott + Flight

    Tarrytown
    3 nights
    4.5 star property
    9.0/10 - Wonderful (692 reviews)
    "Clean room, cute vibes, great restaurants and location to Sleepy Hallow halloween fun!"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - White Plains (HPN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $962
    CA $838
    per traveller
    found 1 day ago
    Westchester Marriott

Where to stay in Stamford

Find the best Stamford areas and neighborhoods for the activities you enjoy most. Learn more about Stamford
Learn more about Stamford
A modern urban area with high-rise buildings, including a distinctive glass facade and a red-brick structure.

Downtown Stamford

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.
A marina with various boats docked, surrounded by rocky shores and a grassy area.

South End

South End combines Stamford's industrial past with modern urban renewal. Former factories now house lofts, studios, and trendy dining spots along tree-shaded streets. The area borders Long Island Sound with scenic Harbour Point waterfront areas and Kosciuszko Park offering beautiful water views. The Stamford Transportation Centre makes this a convenient base for Northeast travel with regular trains to NYC and Boston. Art galleries in converted spaces showcase local creativity. Harbour Point's contemporary towers contrast nicely with the historic brick buildings that tell stories of the area's manufacturing heritage.
A rocky shoreline with clear water reflecting the sky and distant trees.

Cove - East Side - Shippan

Cove - East Side - Shippan showcases the peaceful side of Stamford along picturesque Long Island Sound. West Beach and Cove Island Park offer scenic coastal walks with sandy shores and marina views. This residential haven balances waterfront charm with authentic Connecticut suburban living. Chelsea Piers provides recreation while the area's collection of private marinas highlights its boating culture. Travellers appreciate the quiet tree-lined streets and spacious properties. Though dining options are limited, the neighborhood's natural beauty and waterfront parks make it perfect for those seeking a relaxed coastal experience.
A coastal cityscape with a prominent rocky shoreline and a clear blue sky.

Glenbrook-Belltown

Glenbrook-Belltown offers a peaceful retreat from Stamford's busier areas with tree-lined streets and family-friendly areas. The local train station provides easy access to New York City and Connecticut destinations in under an hour. This budget-conscious area combines suburban charm with transportation convenience. Travellers will appreciate the quiet residential atmosphere and more affordable dining options than downtown. The area serves as an excellent base for exploring nearby attractions like Stamford Centre for the Arts and Chelsea Piers. Small parks and walkable streets make this area perfect for those seeking an authentic suburban experience.
A frozen lake with reflections of trees and reeds.

Springdale

Springdale is a welcoming residential area in Stamford with quiet, tree-lined streets and family-friendly charm. The area centers around its own Metro-North train station, offering easy access to New York City. Visitors can enjoy Sterling Farms Golf Course or explore local shops at Springdale Shopping Centre. The area provides a budget-friendly alternative to downtown Stamford with practical amenities and a relaxed pace. Scalzi Park offers pleasant walking trails and recreation spaces for outdoor enthusiasts. Most local businesses close early, creating a peaceful evening atmosphere perfect for travellers seeking a genuine suburban experience.

Discover the most popular places to visit in Stamford

A city intersection with modern buildings, a church, and a crosswalk.

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.
See properties

What to do in Stamford

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $1,046
per traveller
0% of travellers recommend
Introductory Helicopter Flight Lesson from Westchester
See all activities in Stamford

Stamford Hotel Deals

The entrance of a Marriott Residence Inn with a revolving door, large windows, and a stone facade.

Residence Inn Stamford Downtown

Residence Inn Stamford Downtown
3.0 star property
0.2 km from Stamford
9.4 out of 10, Exceptional, (435 reviews)
The price is CA $377
CA $434 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn Stamford Downtown
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.
See all properties in Stamford

Frequently Asked Questions

How much does a Stamford vacation package cost?

Offering great value package deals from CA $796 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?

  1. Pick your travel dates: What you plan to do in Stamford and your favourite season can help you decide when to get away.
  2. 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.
  3. 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.
  4. Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, book the perfect Stamford vacation package for you.

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