A paved road with a yellow centerline, surrounded by lush greenery and trees.

Kennett Square Vacations from $217

Book a Hotel + Flight or Car together to unlock savings

Your Kennett Square Vacation

Lock in a Kennett Square vacation package that includes everything you need without any unnecessary extras. Good for views, culture and dining, consider basing yourself in the neighborhood of Downtown Wilmington. Make your trip to Kennett Square even more enjoyable by including some sightseeing. Longwood Gardens, Chaddsford Winery and Longwood Cemetery are some of the big attractions you'll want to explore. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Kennett Square now.

The Latest Kennett Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 22 - Jan 24

    Society Hill Hotel + Flight

    Center City
    2 nights
    2.0 star property
    8.0/10 - Very good (111 reviews)
    "Good stay. We got in late and just needed a room so it worked well for us. Felt more like a hostel and I should've seen there was no elevator as we were on the 4th floor. That's on me. The bathroom was great. Heated floors and a Ferrari of a toilet. We were next to a busy street and it was very loud through about 3am but again, we're in the city and that's what you get. Overall no complaints and it's a great area with lots around for food and drink."
    Reviewed November 8, 2026
    Roundtrip • Miami (MIA) - Philadelphia (PHL)
    MIA - PHL • Nonstop PHL - MIA • Nonstop
    $307
    $217
    per traveler
    found 4 hours ago
    Society Hill Hotel
  • Jan 1 - Jan 4

    Orchard Way + Flight

    Yeadon
    3 nights
    2.0 star property
    Roundtrip • Miami (MIA) - Philadelphia (PHL)
    MIA - PHL • Nonstop PHL - MIA • Nonstop
    $2,689
    $1,621
    per traveler
    found 1 day ago
    Orchard Way
  • Jan 22 - Jan 24

    One Sky Loft + Flight

    Center City
    2 nights
    2.0 star property
    9.2/10 - Wonderful (160 reviews)
    "Extremely clean, and a very convenient location. Excellent value for the money."
    Reviewed November 11, 2026
    Roundtrip • Miami (MIA) - Philadelphia (PHL)
    MIA - PHL • Nonstop PHL - MIA • Nonstop
    $320
    $224
    per traveler
    found 4 hours ago
    One Sky Loft
  • Jan 22 - Jan 24

    Fitler Club + Flight

    Center City
    2 nights
    4.0 star property
    9.4/10 - Exceptional (427 reviews)
    "It was amazing!"
    Reviewed November 8, 2026
    Roundtrip • Miami (MIA) - Philadelphia (PHL)
    MIA - PHL • Nonstop PHL - MIA • Nonstop
    $406
    $288
    per traveler
    found 4 hours ago
    Fitler Club
  • Dec 28 - Jan 2

    Hotel Anna & Bel + Flight

    North Philadelphia
    5 nights
    4.0 star property
    9.6/10 - Exceptional (203 reviews)
    Roundtrip • Atlanta (ATL) - Philadelphia (PHL)
    ATL - PHL • Nonstop PHL - ATL • Nonstop
    $1,536
    $1,147
    per traveler
    found 1 day ago
    Hotel Anna & Bel

Where to stay in and around Kennett Square

Kennett Square offers a delightful mix of outdoor adventures and family-friendly activities. Explore the friendly atmosphere of downtown Kennett Square, then venture to nearby Montchanin Village or Doylestown for cultural experiences. For a beach day, Rehoboth Beach is just a short drive away, making it perfect for a refreshing getaway.

Wilmington

Families and weekend getaway travelers will find Wilmington to be the perfect base to explore the rich offerings of Delaware. This vibrant city features attractions like the Wilmington Riverwalk, perfect for leisurely strolls, and the Winterthur Museum, Garden and Library, which provides a glimpse into history and art. With easy access to shopping centers and urban parks, Wilmington is a delightful destination. Located about 11 miles by car from Kennett Square, it's an ideal choice for a memorable stay.

Newark

Experience the charm of Newark, Delaware, an excellent hub for families and weekend getaway travelers who want to immerse themselves in a vibrant city atmosphere. With attractions like the historic University of Delaware, the Bob Carpenter Center, and the Chase Center on the Riverfront, Newark offers a delightful mix of education, entertainment, and culture. Located about 12 miles away from Kennett Square, this lively city is a smart choice for your hotel stay, ensuring easy access to a variety of experiences.

West Chester

If you are a family-oriented traveler or a nature enthusiast, make the most of your visit by staying in West Chester, which features vibrant attractions like West Chester University, the stunning Longwood Gardens, and the Brandywine River Museum. This charming city offers a delightful mix of outdoor experiences and urban conveniences, ensuring you'll find plenty to do. Located about 10 miles away from Kennett Square, West Chester is an excellent choice for your accommodations, providing easy access to all the region has to offer.

Coatesville

Coatesville stands out as a prime spot for travelers seeking a weekend getaway, family fun, or a connection with nature. Visitors can explore stunning attractions like Longwood Gardens, the National Iron and Steel Heritage Museum, and West Chester University, offering a blend of outdoor beauty and cultural experiences. Located about 11 miles by car from Kennett Square, Coatesville provides easy access to these highlights, making it a smart choice for your stay.

Downingtown

Travelers visiting the area often choose Downingtown, especially families and food enthusiasts seeking close proximity to a vibrant mix of experiences. This charming city offers easy access to beautiful attractions like Longwood Gardens, perfect for nature lovers, and the educational environment of West Chester University. With its welcoming parks and shopping at Eagleview Town Center, Downingtown is an ideal base just about 11 miles by car from Kennett Square, making it a smart choice for a memorable vacation.

Discover the most popular places to visit in Kennett Square

Kennett Square Hotel Deals

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.

Frequently Asked Questions

How much does a Kennett Square vacation package cost?

You can grab a vacation package to this top destination from $217 on Expedia. However, how much your vacation to Kennett Square costs will depend on factors like your hotel choice, season and length of stay.

What are the cheapest months to go to Kennett Square?

If you're looking to snag a cheap Kennett Square vacation package, consider traveling in January, May and December. You're likely to find better prices on accommodations and flights during these quieter months — ideal for budget-conscious travelers.

How many days is enough for Kennett Square?

Generally, a few days is ideal for a Kennett Square vacation. With a well-planned itinerary, you can visit all the popular sights such as Longwood Cemetery, as well as explore some hidden gems along the way.

Is it worth booking a vacation package to Kennett Square?

Kennett Square offers everything you need for an amazing escape. Begin your Kennett Square vacation on a high note by checking out major attractions like Longwood Gardens.

How to find the best Kennett Square package deals?

Start your search for a Kennett Square package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kennett Square package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kennett Square getaway off to a flying start.

Is it cheaper to book a Kennett Square vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Kennett Square vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Kennett Square?

If you're planning an impromptu Kennett Square getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.

How to plan a trip to Kennett Square?

  1. Pick your travel dates: What you'd like to do in Kennett Square and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: As well as the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Kennett Square.
  3. Explore Kennett Square using our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Kennett Square. You can also save your favorite locations, collaborate with your group and manage your plans in one place.
  4. Determine how many days away: Start by listing all the sights and activities you'd like to experience in Kennett Square. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, lock in the right Kennett Square vacation package for you.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Kennett Square. Find all the fun things to do in Kennett Square with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Kennett Square vacation packages?

Your Kennett Square getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.