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.
Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown

Downtown Stamford
CA $855
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9/10 Wonderful! (902 reviews)
Delamar Greenwich Harbor

Delamar Greenwich Harbor

CA $1,349
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

Southeast Yonkers
CA $1,082
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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

Delamar Southport

Delamar Southport

CA $1,669
per person
Dec 24 - Dec 28
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.6/10 Exceptional! (517 reviews)
For the price I would expect a higher overall quality of service and accommodations. When we pulled up, there was a luggage cart at the door, but no one was attending to it. There was no valet. A staff member appeared after we rolled the cart to our car in the rain and loaded our luggage onto it ourselves. The room was small and not equipped with a tea or coffee maker. Tea/coffee was supposed to be available with breakfast starting at 7. When my husband went down at 7, the staff was not ready and visibly annoyed when he asked for a tea bag. We had to manually unscrew the drain in the shower to get the water to go down after showering, and when we turned the sink faucet on, water leaked and pooled on the vanity coming from one handle. We ate dinner in the restaurant. The service was very slow. Our food was dropped off by a runner who quickly left. We were halfway through our meal before my husband was able to flag down our waiter to ask for condiments and a refill of our drinks. Overall, our stay wasn't bad. I was excited to stay here, since other Fairfield parents highly recommended it. I just didn't feel it was worth the price.

Reviewed on Oct 3, 2026

Delamar Westport

Delamar Westport

CA $1,705
per person
Dec 24 - Dec 28
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.6/10 Exceptional! (154 reviews)
The experience was wholly lacking and a far cry from what we would expect for the Delamar brand. Positives: clean and comfortable beds/pillows. Negatives: 1) difficulty reaching front desk 2) slow response to complaints 3) no one offered to help with our bags upon check in 3) assigned room was very big and bright but overwhelming MOLD smell. 4) changed rooms with no offered help from staff; they told us yo come to front desk to get new keys 5) new room dark and smaller 6) no water pressure in sinks 7) kept awake by occupant above with thumping across floor. The floors -although pretty-are bare so sound travels. 8) supposedly fab restaurant for dinner was all talk and bluster and quite mediocre. 9) decent looking breakfast buffet- trays were left untended so warm food was cold and bowls of other things lay empty until attendants were told. For close to $400/night, I say “NO THANKS”

Reviewed on Oct 6, 2026

Where to stay in Stamford

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

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.

A waterfront marina with boats, a dock, a grassy area with benches, and urban buildings in the background.

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.

A coastal cityscape with a prominent rocky shoreline and a clear blue sky.

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.

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

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.

A sandy beach with a clear blue sky, a rocky breakwater, and trees in the background.

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?

Choose your dates

Stamford Hotel Deals

Amsterdam Hotel

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT
CA $149
CA $173 total
Nov 7 - Nov 8
includes taxes & fees
Amsterdam Hotel
The Stamford Hotel

The Stamford Hotel

700 East Main Street Stamford CT
Fully refundableReserve now, pay when you stay
CA $237
CA $272 total
Oct 21 - Oct 22
includes taxes & fees
The Stamford Hotel
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2701 Summer St Stamford CT
CA $216
CA $249 total
Oct 18 - Oct 19
includes taxes & fees
The Armon Stamford Hotel & Conference
See all 2,159 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.

Stay near popular Stamford attractions

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.
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A lake surrounded by trees and rocks.

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.
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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.
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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.
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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.
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West Beach

7.6/10 (37 reviews)
Why not spend a lazy afternoon at West Beach during your trip to Stamford?
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Cummings Park Beach

6.4/10 (5 reviews)
Why not spend a lazy afternoon at Cummings Park Beach during your trip to Stamford?
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Sterling Farms Golf Course

6.0/10 (1 review)
Enjoy a round of golf in Stamford at Sterling Farms Golf Course. Discover the lively bars and entertainment choices in this family-friendly area.
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What to do in Stamford

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $1,818
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 $855 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.

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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.