Williamsport Vacations from $355

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Your Williamsport Vacation

Simplify your travel planning by booking a Williamsport vacation package. A great neighborhood to stay in this exciting city is Fountainhead-Orchard Hills, which is great for golfing and a lot more. Maryland Theater, Hagerstown Premium Outlets and Hagerstown Speedway are just some of the many attractions you'll want to explore during your trip to Williamsport. Expedia will help you escape your routine. Tailor your vacation to Williamsport to suit your travel style, whatever that may be.

The Latest Williamsport vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Hancock MD

Super 8 by Wyndham Hancock MD

2 out of 5
Price was $397, price is now $355 per person
$355
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hagerstown (HGR)
7/10 Good! (713 reviews)
The "breakfast" was the biggest joke I've ever seen. Coffee, Milk, OJ. Two sugar cereals. A few donuts. Sum total.

Reviewed on Jul 7, 2026

Stoner's Mansion House

Stoner's Mansion House

2 out of 5
Price was $602, price is now $512 per person
$512
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hagerstown (HGR)
8.6/10 Excellent! (91 reviews)
Window air is annoying all night long but does block out the music

Reviewed on Jul 13, 2026

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
Price was $579, price is now $500 per person
$500
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hagerstown (HGR)
9/10 Wonderful! (1,613 reviews)
The room was clean and the amenities were good.

Reviewed on Jul 12, 2026

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

2 out of 5
The Woods
Price was $651, price is now $605 per person
$605
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hagerstown (HGR)
7/10 Good! (10 reviews)
No pool access, bbq had no gas , broken furniture, light switches in bedrooms did not work, 5 calls to host went unanswered, will request a full refund!!!

Reviewed on Jun 28, 2026

SureStay Plus Hotel by Best Western Berkeley Springs

SureStay Plus Hotel by Best Western Berkeley Springs

2.5 out of 5
Price was $489, price is now $456 per person
$456
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hagerstown (HGR)
8.6/10 Excellent! (1,002 reviews)
Maybe the cleanest hotel I’ve ever stayed in. When I got to my room my air conditioner wasn’t working. After trying a couple times, the desk clerk moved me to an upgraded room. No questions asked. The rooms are spotless - honestly cleaner than some luxury hotels I’ve stayed in. It could use better mattresses and linens, but given the chain and class of hotel they were appropriate. I would stay here again.

Reviewed on Jul 8, 2026

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Stay near popular Williamsport attractions

Williamsport City Hall

This historic building houses Williamsport's administrative center while showcasing the town's heritage. Visitors can appreciate its architecture while exploring the quaint surroundings of Conococheague Street.
See properties

Williamsport Hotel Deals

Red Roof Inn Hagerstown - Williamsport, MD

Red Roof Inn Hagerstown - Williamsport, MD

2 out of 5
310 E Potomac St, Building A Williamsport MD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $96 total per night from Aug 13 to Aug 14
$96 total
Aug 13 - Aug 14
Total with taxes and fees
7.2/10 Good! (978 reviews)
"The rooms needed better housekeeping. The floors were in need of a good mopping. Our daughter’s socks ended up completely black just from walking around for a few minutes. The bedding could have been better as it seemed to have stains on it. I do like that it is pet friendly and the first pet stays ..."

Reviewed on Jul 14, 2026

Red Roof Inn Hagerstown - Williamsport, MD
HomeTowne Studios by Red Roof Hagerstown - Williamsport, MD

HomeTowne Studios by Red Roof Hagerstown - Williamsport, MD

3 out of 5
310 East Potomac Street, Building B Williamsport MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Aug 13 to Aug 14
$85 total
Aug 13 - Aug 14
Total with taxes and fees
HomeTowne Studios by Red Roof Hagerstown - Williamsport, MD
Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
Fully refundable
$101 nightly
The price is $113 total per night from Aug 9 to Aug 10
$113 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (1,292 reviews)
"A pleasant stay in a slightly dated motel. Everything worked fine eerything was comfortable, the shower bath had a nonslip bottom - but only a small, low grab bar. Staff were all very friendly and helpful."

Reviewed on Jul 13, 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 757 properties in Williamsport
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 Williamsport Vacation Packages

Williamsport Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hagerstown Regional Airport (HGR)
Population
2,200
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Greenbrier State Park, Maryland Theater and Crystal Grottoes Caverns

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Frequently asked questions

How much does a Williamsport vacation package cost?
You'll find cheap prices from $355 on Expedia for your Williamsport break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Williamsport costs.
What are the cheapest months to go to Williamsport?
If you'd like to snag a cheap Williamsport vacation package, consider visiting in November, December and January. You'll generally find better rates on accommodations and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Williamsport?
With a well-organized travel plan, you can easily visit the most popular Williamsport sights in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Williamsport vacation for longer.
How to find the best Williamsport package deals?
Use Expedia's filter tool to help you find some tempting Williamsport package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Williamsport package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Williamsport vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Williamsport vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Williamsport?
If you've got your Williamsport travel dates finalized, book early to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Williamsport vacation packages?
Your Williamsport break should be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.