How much does a Stamford vacation package cost?

You'll find cheap prices from $243 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.

Stamford Vacation Packages 2025/2026 from $243

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.

Hilltop Inn & Suites

Northwest Yonkers

$243

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

6.8/10 (316 reviews)

Renovations going on but clean safe and comfortable. I was delayed at airport got in late. They were waiting and happy to welcome me. Very nice place

Reviewed on Aug 11, 2025

Luxury NY Home 3BR with Easy Parking

Southeast Yonkers

Save 100% on your flight

$1,776

per person

Oct 28 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to White Plains (HPN)

3/10 (4 reviews)

Hampton Inn White Plains/Tarrytown

$611

per person

Oct 28 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to White Plains (HPN)

8/10 Very Good! (1,092 reviews)

Everything was fine. The only issue is the toilet is very low. A little difficult for someone with knee issues.

Reviewed on Aug 20, 2025

Sleepy Hollow Hotel

$765

per person

Oct 28 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to White Plains (HPN)

6.6/10 (1,013 reviews)

The staff was very very helpful/kind/responsive!!!

Reviewed on Aug 18, 2025

Global Luxury Suites White Plains

Save 100% on your flight

$588

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Miami (MIA) to White Plains (HPN)

6.8/10 (31 reviews)

Nice view from the apartment and great for business trip.

Reviewed on Dec 16, 2024

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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

Downtown Stamford

2 out of top 10 points of interest in this area

4/5(199 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.

Stamford Hotel Deals

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Fully refundableReserve now, pay when you stay

$100 nightly

$116 total

Aug 24 - Aug 25

Total includes taxes and fees

8.4/10 Very Good! (1,637 reviews)

"Good deal for the price. Room clean, staff always pleasant, professional and helpful"

Reviewed on Aug 19, 2025

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

135 Harvard Avenue, Stamford, CT

Fully refundableReserve now, pay when you stay

$90 nightly

$104 total

Sep 11 - Sep 12

Total includes taxes and fees

6.4/10 (729 reviews)

"My experience was ok but there need update coffee maker in room"

Reviewed on Aug 18, 2025

The Stamford Hotel

700 East Main Street, Stamford, CT

Fully refundableReserve now, pay when you stay

$178 nightly

$205 total

Aug 28 - Aug 29

Total includes taxes and fees

7.8/10 Good! (1,109 reviews)

"I have stayed here before and I always enjoy my night there. The staff are always friendly and welcoming. The bar is wonderful the guy there is so friendly and always makes these amazing drinks. I’m"

Reviewed on Aug 20, 2025

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.

Things to do in and around Stamford

Stamford, Connecticut, offers a variety of activities perfect for families and outdoor enthusiasts. Enjoy shopping in vibrant areas, catch a show at the theater, or embark on educational excursions. Key experiences include exciting day trips, engaging class trips, and scenic walking tours that highlight the city's charm. Whether you're exploring the bustling downtown or enjoying the beautiful parks, Stamford promises a memorable vacation.

Shopping

Stamford Town Center offers a vibrant shopping experience with various stores and entertainment options. Springdale Shopping Center features a mix of shops and family-friendly vibes. If you're up for a drive, Goldenberry, located 7 miles away, is a charming store perfect for unique gifts and souvenirs.

Recreation

At Chelsea Piers, engage in a variety of sports activities in a vibrant atmosphere, perfect for fitness enthusiasts. Experience the cultural richness at Stamford Center for the Arts, where theater meets entertainment. Unwind at Hand & Stone Massage and Facial Spa, a serene retreat offering soothing massages and rejuvenating facials.

Adventure

Experience the wonders of Legoland Discovery Center Westchester, located 18 miles from Stamford, where adventure awaits families with its interactive exhibits and rides. For thrill-seekers, Grand Prix New York offers exciting karting 15 miles away, while Sportime USA, 14 miles from Stamford, combines arcade fun with family-friendly vibes.

Nightlife

In Stamford, Connecticut, experience vibrant nightlife at Harbor Point, featuring chic bars and waterfront dining. Explore downtown for lively pubs and music venues. Don’t miss the Palace Theatre for live performances, and enjoy late-night bites at local eateries for a perfect night out.

*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, offers a perfect blend of family-friendly activities, urban parks, and beautiful beaches for outdoor enthusiasts. Visitors can explore a variety of points of interest that cater to outdoor adventures, cultural experiences, and family fun. Whether you're looking to relax by the beach or enjoy a day in a scenic park, Stamford has something to make your vacation memorable.

Greenwich Avenue: Experience the vibrant city atmosphere of Greenwich Avenue, located 5 miles from Stamford. This bustling street offers a mix of upscale shops, trendy cafes, and art galleries, perfect for a leisurely stroll or shopping spree.
Rye Playland: Just 9 miles away, Rye Playland is a classic amusement park that promises fun for the whole family. With thrilling rides and games, it’s an ideal place for adventure seekers and those looking to create lasting memories.
Cove Island Park: Situated within Stamford, Cove Island Park is a beautiful urban park featuring scenic walking trails, picnic areas, and stunning waterfront views. It’s a perfect spot for families to enjoy outdoor activities while soaking in the city vibes.

Best time to go to Stamford

The best time to visit Stamford is dependant 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 during the off-peak season (typically January to March) for more affordable package holidays to Stamford.
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.