Stratford Vacation Packages 2026 from $533

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Your Stratford Vacation

Prepare to experience Stratford in your own style with a custom Stratford vacation package! Discovering the best parts of this interesting city is simpler with a base in a neighborhood such as Lordship, which is great for coastal beaches, among lots of other things. Fill your free time with tours of Total Mortgage Arena, Hartford HealthCare Amphitheater and Jennings Beach, some of the attractions you really should see during your trip to Stratford. Expedia is here to help you escape the everyday. Tailor your vacation to Stratford to match your travel style, whatever that may be.

The Latest Stratford vacation packages

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

Landing Furnished Apartment Near Yale University

Downtown New Haven

$533

per person

Oct 30 - Nov 2

found 15 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to New Haven (HVN)

2/10 (1 review)

Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent

Reviewed on Sep 14, 2026

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$788

per person

Dec 11 - Dec 13

found 21 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to New Haven (HVN)

No reviews

Head of Pond House

$661

per person

Nov 8 - Nov 11

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

10/10 Exceptional! (13 reviews)

The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.

Reviewed on Sep 23, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$563

per person

Oct 30 - Nov 2

found 15 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to New Haven (HVN)

9.6/10 Exceptional! (88 reviews)

Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”! I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!

Reviewed on Sep 18, 2026

Omni New Haven Hotel at Yale

Downtown New Haven

$683

per person

Nov 8 - Nov 11

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

8.6/10 Excellent! (1,088 reviews)

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Stay near popular Stratford attractions

A rocky shoreline with a calm sea and a cloudy sky.

Lordship Beach

9.0/10 (7 reviews)

Lordship Beach offers a tranquil stretch of Connecticut shoreline with sweeping views of Long Island Sound. Bring a picnic and spend a peaceful afternoon watching sailboats drift across the water.

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A lifeguard chair with a sign that reads "NO LIFEGUARD ON DUTY" on a beach with calm water and a clear sky.

Short Beach

8.6/10 (17 reviews)

This serene shoreline at the Housatonic River's mouth offers a perfect blend of relaxation and recreation. Enjoy the sandy beach, sports facilities, and family-friendly picnic areas with Long Island Sound views.

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Boothe Memorial Park and Museum

9.0/10 (12 reviews)

This historic park showcases unique architectural treasures including a clock tower and blacksmith shop. Stroll through blooming gardens and discover the Boothe Homestead's fascinating artifacts during your visit.

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A beach with rippled sand patterns and a sunset sky.

Long Beach

8.6/10 (7 reviews)

Long Beach offers 1.5 miles of unspoiled Connecticut coastline where shorebirds nest in protected dunes. Enjoy the natural serenity with swimming and sunbathing—just remember to bring your own beach essentials.

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Stratford Speedway

You can take time to visit Stratford Speedway during your travels to Stratford. While in this family-friendly area, you can savor the top-notch restaurants.

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Stratford Historical Society Capt David Judson House

8.4/10 (7 reviews)

This historic 18th-century residence showcases colonial Connecticut life with original architecture and period furnishings. Explore Captain Judson's era during a guided tour of this well-preserved landmark.

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Perry House

8.6/10 (8 reviews)

The Perry House, a historic Stratford homestead, showcases Connecticut's heritage through period furnishings and artifacts. Explore its cultural exhibits and educational workshops that bring local history to life.

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Academy Hill

8.6/10 (4 reviews)

Academy Hill showcases three centuries of Stratford's evolution through Federal townhouses, Greek Revival villas, and colonial homesteads. Stroll the tree-lined streets of this preserved New England seaport town.

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Stratford Hotel Deals

Quality Suites Stratford

1500 South Ave Stratford CT

Fully refundable

$107 nightly

$123 total

Oct 18 - Oct 19

Total with taxes and fees

8.2/10 Very Good! (1,005 reviews)

"Very nice people made this a nice hotel."

Reviewed on Sep 25, 2026

Homewood Suites by Hilton Stratford

6905 Main St Stratford CT

Fully refundableReserve now, pay when you stay

$152 nightly

$175 total

Oct 4 - Oct 5

Total with taxes and fees

8.8/10 Excellent! (1,003 reviews)

"The value is great considering the size of the room and the efficiency living elements -- frig, elec stovetop, micro wave, sink, cups, saucers, utensils and paper towels. The only downside is that the air conditioning/heating emitted a harsh smell when put on heat. Otherwise, the air conditioning ..."

Reviewed on Sep 24, 2026

The Surfside Hotel

10 Washington Pkwy Stratford CT

Fully refundableReserve now, pay when you stay

$215 nightly

$247 total

Oct 13 - Oct 14

Total with taxes and fees

9.2/10 Wonderful! (222 reviews)

"Beautiful ocean front location. Private Sandy Beach. Clean and well maintained. Great onsite pub and restaurant. We enjoyed our stay so much!"

Reviewed on Sep 16, 2026

See all 1,241 properties in Stratford

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 Stratford Vacation Packages

Things to do near Stratford

Stratford, Connecticut, is perfect for outdoor and family-oriented vacations, offering a variety of activities. Visitors can explore local attractions, enjoy theatre performances, attend music concerts, and participate in community events. The area also features beautiful beaches and scenic waterfalls, making it an ideal spot for relaxation and adventure. Whether you're looking to unwind at a resort or immerse yourself in cultural experiences, Stratford has something for everyone.

Shopping

The nearest shopping destination is Westfield Connecticut Post Mall, located 6 miles away, offering a vibrant mix of entertainment and family-friendly options. Milford Plaza Shopping Center, also 6 miles away, features a variety of shops. If you're up for a drive, check out Westport Farmers Market, 12 miles from Stratford.

Recreation

Experience vibrant performances at the Downtown Cabaret Theatre, perfect for family entertainment and cultural immersion. Unwind at Seaside Park, where you can enjoy nature and relaxation. For sports enthusiasts, the Hartford HealthCare Amphitheater offers an exciting atmosphere just a short drive away, enhancing your wellness journey.

Adventure

The Adventure Park at Discovery Museum, 6 miles from Stratford, offers thrilling zipline and ropes courses amidst scenic outdoor vibes. Experience the whimsical Lighthouse Point Carousel, 13 miles away, perfect for family fun. For water enthusiasts, Waterski Connecticut, located 11 miles away, provides exhilarating water sports adventures.

Nightlife

Stratford offers a vibrant nightlife with venues like the popular Stratford Theater for live performances and the lively Crazy Bruce's for drinks. For a more relaxed vibe, visit local pubs like the Half Door, where you can enjoy craft beers and good company.

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

Find the best attractions near Stratford

Stratford, Connecticut, offers a delightful vacation for families and outdoor enthusiasts alike. Visitors can enjoy beautiful beaches, explore historic colleges and universities, and relax in urban parks. With a rich cultural scene, Stratford attracts travelers seeking a mix of outdoor experiences and local history. Don't miss the Stratford Festival for a taste of the region's vibrant arts scene while you're in town.

Yale University: Located 14 miles from Stratford, Yale University is an iconic institution steeped in history and culture. Explore its stunning Gothic architecture, visit the Yale University Art Gallery, and stroll through the beautiful campus, immersing yourself in the vibrant academic atmosphere.
Silver Sands State Park: Just 4 miles away, Silver Sands State Park offers a perfect blend of adventure and stunning scenery. Enjoy hiking trails, sandy beaches, and picturesque views of the Long Island Sound, making it an ideal spot for outdoor enthusiasts and nature lovers alike.
Bridgeport Downtown South Historic District: Only 3 miles from Stratford, this historic village boasts charming streets filled with cultural sites, local shops, and eateries. Experience the rich heritage and artistic vibe as you explore the area’s unique architecture and vibrant community events.

Best time to go to Stratford

The best time to visit Stratford can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Stratford falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Stratford falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.8°F (-0.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	32.9°F (0.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	39.0°F (3.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	48.9°F (9.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.8°F (14.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
June	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	74.8°F (23.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Average	Average
September	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Average
October	57.4°F (14.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	46.2°F (7.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Stratford

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Stratford 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.

Stratford Beach Vacation

Listen to the soothing sound of waves lapping at the shore and kick back by the glistening waters during your Stratford vacation. If you're in need of some time out, a trip to Stratford is your ticket to relaxation. We have plenty of Stratford vacation deals to pick from. Snap up one near Short Beach, just 2 miles (4 km) from the center of town, and live out your vacation fantasies without hurting your budget.

Stratford Essential Information

Language	English
Currency	U.S dollars
Closest Airport	MacArthur Airport (ISP)
Population	51,400
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	Jennings Beach, Beardsley Zoo and Seaside Beach

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Frequently asked questions

How much does a Stratford vacation package cost?

You can pick up a vacation package to this destination from $533 on Expedia. But how much your vacation to Stratford costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Stratford?

You can typically find reduced prices and better availability in January, May and November. Take a look at our cheap Stratford vacation packages and you could land some great off-season discounts.

How many days is enough for Stratford?

Allow at least 2 days for your Stratford vacation to really immerse yourself in everything that makes this place special. Wander around popular neighborhoods, including East End and Lordship. Then make a beeline for top sights such as Academy Hill and Boothe Memorial Park and Museum. With a well-planned itinerary, you'll be kept busy with room for some rest and relaxation too. Want to go beyond Stratford? Consider an excursion or two.

Is it worth booking a vacation package to Stratford?

Known for its coastal beaches and home to leading attractions like Short Beach, a Stratford vacation is bound to impress. Another highlight to check out? Don't miss Perry House.

How to find the best Stratford package deals?

Use Expedia's filter tool to find some tempting Stratford package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Stratford package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.

Is it cheaper to book a Stratford vacation as a package?

An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can customize your Stratford trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a vacation package to Stratford?

If you're planning an impromptu Stratford vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.

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

Secure your ideal getaway to Stratford with help from our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up travel deals before they sell out.

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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.

Stratford Vacations from $533

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Stratford Vacation

The Latest Stratford vacation packages

Landing Furnished Apartment Near Yale University

Beechmont - Perfect for Family Retreat!

Head of Pond House

Luxury Furnished Apartments by Hyatus Downtown at Yale

Omni New Haven Hotel at Yale

Stay near popular Stratford attractions

Lordship Beach

Short Beach

Boothe Memorial Park and Museum

Long Beach

Stratford Speedway

Stratford Historical Society Capt David Judson House

Perry House

Academy Hill

Stratford Hotel Deals

Quality Suites Stratford

Homewood Suites by Hilton Stratford

The Surfside Hotel

Find the Best Stratford Vacation Packages

Things to do near Stratford

Find the best attractions near Stratford

Best time to go to Stratford

Tips to save on your trip to Stratford

Stratford Beach Vacation

Stratford Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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