Woodside Vacations from $1,370

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Your Woodside Vacation

Take the hard work out of travel planning by booking a Woodside vacation package. A good neighborhood to stay in this amazing city is Kitts Hummock, which is good for nature and much more besides. Like to venture out and explore? Greentree Village Shopping Center, Rodney Village Shopping Center and Dover Street Park are just three of the best places to visit during a trip to Woodside. Whoever you're escaping with and whatever your bank balance, your dream Woodside vacation is just clicks away with Expedia.

The Latest Woodside vacation packages

Price found within the past 48 hours. Click for updated prices.
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
South Philadelphia
Price was $2,382, price is now $1,370 per person
$1,370
per person
May 10 - May 15
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
9.8/10 Exceptional! (69 reviews)
Lovely space to stay!

Reviewed on Oct 26, 2025

Tudor Place

Tudor Place

4 out of 5
Price was $4,322, price is now $2,342 per person
$2,342
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philadelphia (PHL)
No reviews
Orchard Way

Orchard Way

2 out of 5
Price was $3,345, price is now $2,027 per person
$2,027
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philadelphia (PHL)
No reviews
The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Save 100% on your flight
Price was $3,262, price is now $2,153 per person
$2,153
per person
Jun 24 - Jun 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.6/10 Exceptional! (981 reviews)
Great hotel in rittenhouse square.

Reviewed on Apr 1, 2026

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Discover the most popular places to visit in Woodside

Dover International Speedway

Dover International Speedway

4.5/5(69 reviews)

Catch an event at Dover International Speedway during your trip to Dover. Add the area's shops or casinos to your travel plans.

Dover International Speedway
Cherry blossoms frame the cupola on the roof of the Delaware City Hall in Delaware County, Ohio

Delaware State University

4.5/5(30 reviews)

Walk around the campus at Delaware State University during your visit to Dover. Add the area's casinos or shops to your travel plans.

Delaware State University
American military airf orce transport aircraft departing an air base.

Dover Air Force Base

Dover Air Force Base is just one of the places to see in Dover, so why not enjoy the other things to explore during your travels? Visit the shops and casinos in this family-friendly area.

Dover Air Force Base

Woodside Hotel Deals

Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $107 total per night from Apr 12 to Apr 13
$107 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (3,472 reviews)
Excellent upscale hotel with lots of amenities on site. It is also a great value if you avoid weekends.

Reviewed on Apr 8, 2026

Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
1703 E Lebanon Rd Dover DE
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $84 total per night from Apr 14 to Apr 15
$84 total
Apr 14 - Apr 15
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
The room was nice and clean staff was great the room was big plenty of space my next visit I be staying here again

Reviewed on Apr 5, 2026

Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

2 out of 5
652 N Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Apr 12 to Apr 13
$84 total
Apr 12 - Apr 13
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
Clean

Reviewed on Apr 7, 2026

Red Roof Inn & Suites Dover Downtown
See all 180 properties in Woodside
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 Woodside Vacation Packages

Woodside Essential Information

Language
English
Currency
U.S dollars
Population
2,300
Top Sights
Air Mobility Command Museum, The State House Museum and Biggs Museum of American Art

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Frequently asked questions

How much does a Woodside vacation package cost?
You'll find cheap prices from $1,370 on Expedia for your Woodside getaway. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Woodside costs.
What are the cheapest months to go to Woodside?
November, December and January are great times to look for cheap Woodside vacation packages. Opting to travel in quieter periods means you can generally find lower prices on accommodations and flights.
How many days is enough for Woodside?
Typically, a handful of days is enough to see the major attractions during your Woodside vacation. But if you prefer to have some time to relax or go on day tours, think about extending your itinerary.
How to find the best Woodside package deals?
Use Expedia's handy filters to help you find some fabulous Woodside package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Woodside package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Woodside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Woodside vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Woodside?
If you're considering an impromptu Woodside getaway, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Woodside vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Woodside vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.