Stamford Vacation Packages 2026 from $589

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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.

The Latest Stamford vacation packages

Price found within the past 48 hours. Click for updated prices.

Stanton House Inn

$589

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

9.6/10 Exceptional! (178 reviews)

3BR Prime Luxury NY - Free Parking

Save 100% on your flight

$1,479

per person

Dec 11 - Dec 14

just found

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

6/10 (1 review)

Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected.

Reviewed on Mar 30, 2026

Uscale 2BR Escape in the Heart of NYC

Bryn Mawr

$635

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

9/10 Wonderful! (2 reviews)

Danbury Inn & Suites

$786

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to White Plains (HPN)

4.4/10 (5 reviews)

Delamar Greenwich Harbor

$1,027

per person

Dec 11 - Dec 14

just found

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

9.4/10 Exceptional! (1,002 reviews)

The property was strikingly beautiful, well maintained, very efficient and pleasant staff and the restaurant L’scala was well run and excellent presentation and food quality

Reviewed on Sep 14, 2026

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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

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

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 West Beach and Chelsea Piers.

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 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 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 Stamford Town Center.

Stay near popular Stamford attractions

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

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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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Stamford Hotel Deals

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Fully refundableReserve now, pay when you stay

$89 nightly

$103 total

Oct 8 - Oct 9

Total with taxes and fees

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

135 Harvard Avenue Stamford CT

Fully refundableReserve now, pay when you stay

$91 nightly

$104 total

Oct 18 - Oct 19

Total with taxes and fees

6.6/10 (1,718 reviews)

"It was under construction so understandable that not as clean as it could have been...the weekday breakfast was OK, with scrambled eggs being a touch above simple continental breakfast. A/C unit "fan always on" button didn't work so the A/C kept turning on and off all night not making sleep that ..."

Reviewed on Sep 17, 2026

The Stamford Hotel

700 East Main Street Stamford CT

Fully refundableReserve now, pay when you stay

$176 nightly

$203 total

Oct 18 - Oct 19

Total with taxes and fees

See all 2,162 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.

Find the Best Stamford Vacation Packages

Things to do in and around Stamford

Stamford, Connecticut offers a perfect blend of family-friendly activities and urban exploration. Visitors can enjoy a vibrant shopping area, catch a show at local theaters, or participate in educational outings. Key experiences include guided walking tours, exciting day trips, and class trips that showcase the city’s charm and attractions. Whether you’re seeking outdoor adventures or city-themed fun, Stamford has something for everyone.

Shopping

Stamford Town Center offers a vibrant shopping experience with a mix of entertainment and dining options. For a more local vibe, visit Springdale Shopping Center, perfect for families. If you're up for a drive, check out the Westport Farmers Market, 11 miles away, featuring fresh goods and local businesses.

Recreation

Experience the excitement at Chelsea Piers with various sports activities, indulge in cultural performances at Stamford Center for the Arts, or unwind with soothing treatments at Hand & Stone Massage and Facial Spa. Enjoy a perfect blend of fitness, entertainment, and relaxation in Stamford.

Adventure

Explore the Legoland Discovery Center Westchester, located 18 miles from Stamford, where family-friendly adventures await through interactive attractions and creative play. Experience the thrill of karting at Grand Prix New York / Spins Bowl, 15 miles away, or enjoy arcade fun at Sportime USA, 14 miles from Stamford.

Nightlife

Stamford's nightlife offers a vibrant scene with venues like the lively Harbor Point and the chic downtown bars. Explore the bustling atmosphere at the Stamford Town Center or enjoy live music at local spots, where a mix of cocktails and entertainment keeps the energy high throughout the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Stamford

Stamford, Connecticut, is a fantastic destination for family outings and outdoor adventures. This vibrant city features popular attractions such as beautiful beaches, urban parks, and nature preserves, making it ideal for travelers seeking a mix of outdoor fun and cultural experiences. Whether you're looking to relax by the shore or explore the local parks, Stamford has something to offer for everyone in your family.

Greenwich Avenue: Experience the vibrant city vibes of Greenwich Avenue, located 5 miles from Stamford. This bustling street is known for its upscale shops, trendy cafes, and lively atmosphere, perfect for a leisurely stroll or shopping spree.
Rye Playland: Just 9 miles away, Rye Playland is a classic amusement park that offers family-friendly fun and adventure. With thrilling rides, games, and outdoor attractions, it's an ideal destination for a day of excitement and laughter.
Cove Island Park: Situated within Stamford, Cove Island Park is a beautiful urban retreat featuring scenic waterfront views, walking trails, and picnic areas. Enjoy a relaxing day outdoors with family, surrounded by nature and city vibes.

Best time to go to Stamford

The best time to visit Stamford is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.6°F (-0.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	32.9°F (0.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	39.4°F (4.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	49.6°F (9.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	59.7°F (15.4°C)	Light Rain	Mostly Sunny	Average	Average
June	68.7°F (20.4°C)	Light Rain	Mostly Sunny	Average	Average
July	75.7°F (24.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	74.5°F (23.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.8°F (19.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	57.6°F (14.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	46.2°F (7.9°C)	Light Rain	Mostly Sunny	Average	Average
December	38.1°F (3.4°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High

Tips to save on your trip to Stamford

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Stamford.
Consider traveling to Stamford during the low season (January to March) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Stamford Essential Information

Language	English
Currency	U.S dollars
Closest Airport	John F. Kennedy Intl. Airport (JFK)
Population	128,900
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	Norwalk Maritime Aquarium, Compo Beach and The Maritime Aquarium

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Frequently asked questions

How much does a Stamford vacation package cost?

You'll find cheap prices from $589 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?

You can generally find lower prices and better availability in January, February and March. Take a look at our cheap Stamford vacation packages and you could land some great off-season discounts.

How many days is enough for Stamford?

With about 2 days, you'll have plenty of time to visit popular neighborhoods like Downtown Stamford and Cove - East Side - Shippan during your Stamford vacation. Make sure to also add Cummings Park Beach and Stamford Historical Society Museum to your sightseeing itinerary. Searching for more adventures? Consider venturing outside of Stamford on tours and day trips.

Is it worth booking a vacation package to Stamford?

Stamford offers everything you need for an unforgettable getaway. Get your Stamford vacation off to a flying start by checking out major attractions like Chelsea Piers.

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 the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to travel to Stamford.
Plan your budget wisely: In addition to the cost of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may crop up during your trip to Stamford.
Use our trip planning tool to discover Stamford: Research every part of your trip to Stamford with this handy planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings.
Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Stamford. Then, estimate how long you'll need at each, including any travel time.
Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Stamford vacation package that brings all your bookings together.
Book any activities or excursions: Now to the fun part — locking in everything you want to do and see. Check out some of the exciting things to do in Stamford and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Stamford vacation packages?

Your Stamford break should be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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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.

Stamford Vacations from $589

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Stamford Vacation

The Latest Stamford vacation packages

Stanton House Inn

3BR Prime Luxury NY - Free Parking

Uscale 2BR Escape in the Heart of NYC

Danbury Inn & Suites

Delamar Greenwich Harbor

Where to stay in Stamford

Downtown Stamford

Cove - East Side - Shippan

South End

Waterside

West Side

Stay near popular Stamford attractions

Stamford Town Center

Cove Island Park

Chelsea Piers

Stamford Center for the Arts

West Beach

Hand & Stone Massage and Facial Spa

Cummings Park Beach

Curtain Call

Stamford Hotel Deals

Amsterdam Hotel

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

The Stamford Hotel

Find the Best Stamford Vacation Packages

Things to do in and around Stamford

Find the best attractions in and around Stamford

Best time to go to Stamford

Tips to save on your trip to Stamford

Stamford Essential Information

More vacations you might like

Frequently asked questions

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