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.
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
per person
Sep 13 - Sep 15
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.8/10 (31 reviews)
Nice view from the apartment and great for business trip.

Reviewed on Dec. 16, 2024

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
8.6/10 Excellent! (1,096 reviews)
Everything was fantastic bed was super comfy. Great room service. Only issue, one of the pool attendants vomited into a poolside waste paper basket as I started swimming around 9pm night before I checked out, he left it there said nothing then rested on the job, I immediately went to my room. In all my years that's never happened before. I felt more could have been done by the hotel to apologize.

Reviewed on Aug. 3, 2025

Amsterdam Hotel

Amsterdam Hotel

2 out of 5
Downtown Stamford
per person
Sep 19 - Sep 25
found 10 hours ago
Roundtrip flight included
Montreal (YUL) to White Plains (HPN)
8.4/10 Very Good! (1,628 reviews)
The Amsterdam is an average hotel. Try to avoid rooms on the south side as they face I-95 and you can hear the noise from the road. The continental breakfast goes quickly, so get there early if you want it.

Reviewed on Aug. 5, 2025

Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
6.6/10 (1,013 reviews)
Pros: clean and spacious room. Across the street from a bus stop. Cons: I did not know that if you don't reserve a room directly from their site (for double the price) you don't get any breakfast. You have to buy from their restaurant. No free food whatsoever. Also, I found the whole hotel too brown. Everything in the room and hotel is brown and could use upgrades. I also was told there are walking paths ... There isn't. The pool was not heated and sauna not working.

Reviewed on Aug. 7, 2025

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
per person
Sep 22 - Sep 24
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (927 reviews)
Amazing classy quiet and clean

Reviewed on Aug. 5, 2025

Where to stay in Stamford

Find the best Stamford areas and neighborhoods for the activities you enjoy most. Learn more about Stamford
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Downtown Stamford

2 out of top 10 points of interest in this area
4.5/5(2 area reviews)

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.

Find hotels in Downtown Stamford

Ready to book your vacation to Stamford?

 

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Stamford Hotel Deals

Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Aug 13 to Aug 14
CA $112
CA $130 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very Good! (1,628 reviews)
"Nice place @ a good price"

Reviewed on Aug. 5, 2025

Amsterdam Hotel
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Aug 13 to Aug 14
CA $120
CA $138 total
Aug 13 - Aug 14
includes taxes & fees
6.4/10 (684 reviews)
"Liked breakfast buffet. Did not like fitness room not yet opened."

Reviewed on Aug. 5, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
700 East Main Street, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Aug 18 to Aug 19
CA $187
CA $215 total
Aug 18 - Aug 19
includes taxes & fees
7.6/10 Good! (1,092 reviews)
"Very clean rooms. Friendly service! I would go back"

Reviewed on Aug. 2, 2025

The Stamford Hotel
See all 2,023 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Stamford

Springdale Shopping Center

You can browse for the perfect souvenirs at Springdale Shopping Center during your stay in Stamford. Discover the lively bars and entertainment choices in this family-friendly area.

Springdale Shopping Center

What to do in Stamford

Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

CA $1,302
per traveller
Couple's Private NYC Helicopter Tour from Westchester
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $918
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Stamford

Frequently asked questions

How much does a Stamford vacation package cost?
Offering great value package deals from CA $654 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.