Stamford Vacations from $706

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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.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

Southeast Yonkers
$706
per person
Oct 30 - Nov 1
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Greenwich Harbor

Delamar Greenwich Harbor

Save 100% on your flight
$1,256
per person
Oct 8 - Oct 12
found 9 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
9.4/10 Exceptional! (1,005 reviews)
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

Southeast Yonkers
Save 100% on your flight
$2,023
per person
Nov 5 - Nov 9
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
3/10 (4 reviews)
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

Save 100% on your flight
$2,637
per person
Nov 5 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
8/10 Very Good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on Nov 8, 2025

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

Southeast Yonkers
Save 100% on your flight
$1,775
per person
Oct 30 - Nov 1
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
4.6/10 (11 reviews)
The property that I paid for 1st, they told me that the pipe busted after I paid the cleaning fee. I paid for a property to sleep 6 people so 1 person had to sleep on the floor & another person had to sleep on a broken futon couch. The bed I was sleeping on was broken & there was pee stains on sheet & blanket. I asked them for a discount because of the unexpected things my family went through & they stopped communicating with me until the next day. But do not get any property rental from these people. And they have so many bad reviews I don’t see how Expedia has them on there. I traveled from Ohio & it was my last night in New York & that’s how I spent it. Please take head to this review & the other ones. They weren’t lying.

Reviewed on Aug 17, 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 Cummings Park Beach and West Beach.

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.

Cummings Park Beach in Stamford Connecticut along Westcott Cove

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.

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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A lake surrounded by trees and rocks.

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

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

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

135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
$88 nightly
$102 total
Sep 20 - Sep 21
Total with taxes and fees
6.6/10 (1,681 reviews)
"First room offered smelled badly of cigarette smoke. Second room had no desk chair"

Reviewed on Aug 30, 2026

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

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$98 nightly
$114 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (1,785 reviews)
"Clean room Just a little date but did the job Plenty of free parking and free Breakfast from 7-10am"

Reviewed on Aug 30, 2026

Amsterdam Hotel
Red Carpet Inn

Red Carpet Inn

1209 E Main St Stamford CT
Fully refundableReserve now, pay when you stay
$73 nightly
$84 total
Sep 14 - Sep 15
Total with taxes and fees
Red Carpet Inn
See all 2,172 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly SunnySlightly LowSlightly Low
February32.9°F (0.5°C)Light RainMostly SunnySlightly LowSlightly Low
March39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low
April49.6°F (9.8°C)Light RainMostly SunnySlightly LowAverage
May59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
June68.7°F (20.4°C)Light RainMostly SunnyAverageAverage
July75.7°F (24.3°C)Light RainMostly SunnySlightly HighAverage
August74.5°F (23.6°C)Light RainMostly SunnySlightly HighAverage
September67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
October57.6°F (14.2°C)Light RainMostly SunnyAverageSlightly High
November46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
December38.1°F (3.4°C)Light RainMostly SunnySlightly HighSlightly 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 $706 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.