Dover Vacations

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Your Dover Vacation

Say bye-bye to planning hassles and hello to a Dover vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with South Riding, which is good for hiking, golfing and walking. Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards are just some of the many sights you'll want to see during your trip to Dover. A few clicks is all it takes to create the perfect Dover vacation on Expedia.

Discover the most popular places to visit in Dover

Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

Glenwood Park

5/5(1 review)

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Glenwood Park
Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Red Fox Fine Art

Greenhill Winery & Vineyards

3.5/5(3 reviews)

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this trendy area.

Greenhill Winery & Vineyards

What to do in Dover

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

$90
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

$120
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
See all activities in Dover

Dover Hotel Deals

Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (1,725 reviews)
Rooms were clean staff excellent

Reviewed on May 7, 2026

Hyatt Regency Dulles International Airport
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $302 total per night from May 25 to May 26
$302 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Always a great stay!

Reviewed on Apr 26, 2026

Lansdowne Resort and Spa
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd Herndon VA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $132 total per night from May 30 to May 31
$132 total
May 30 - May 31
Total with taxes and fees
8.4/10 Very Good! (2,872 reviews)
Fire alarm went off at 3:30 am. Broken water line. No water, no hot water for showers in morning

Reviewed on May 7, 2026

Hyatt Place Herndon Dulles Airport East
See all 746 properties in Dover
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 Dover Vacation Packages

Dover Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Top Sights
Greenhill Winery & Vineyards, Chrysalis Vineyards and Cana Vineyards and Winery

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Frequently asked questions

How much does a Dover vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Dover costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Dover?
If you're hoping to score a cheap Dover vacation package, consider visiting in November, December and January. You'll typically find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Dover?
With a well-organized travel plan, you can easily tick off the top Dover attractions in a few days. But if you want to discover hidden gems or go on day tours, consider booking your Dover vacation for longer.
How to find the best Dover package deals?
Start your search for a Dover package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Dover package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Dover adventure underway.
Is it cheaper to book a Dover vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Dover vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Dover?
If you've got your Dover vacation dates finalized, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Dover vacation packages?
Secure your perfect escape to Dover with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.