Pittsville Vacations from $1,229
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Your Pittsville Vacation
Our Pittsville vacation packages allow you to customize your own adventure. Tailor your journey to your interests and needs and make the most of your time in this wonderful city. Any trip to Pittsville should include some sightseeing. Wor-Wic Community College is an excellent place to kick things off. Don't delay exploring this city any longer. The ultimate Pittsville vacation is only a few clicks away with Expedia.
The Latest Pittsville vacation packages
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Downtown Ocean City
$1,616
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (107 reviews)
The property needs some TLC. And the beds we're re-made with the same sheets. Sheets we're dirty with spots on them. Im glad I brought my own blankets and
Reviewed on Aug 17, 2026
Majestic Hotel & Apartments
Downtown Ocean City
$1,707
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
6/10 (461 reviews)
Room was very small. No hot water in bathroom. Had to find linen closet for clean towels and sheets. Had to change our own linens. Staff was not helpful at all.
Reviewed on Aug 18, 2026
Plim Plaza Hotel
Downtown Ocean City
$1,427
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.4/10 Good! (1,109 reviews)
My room had a smell the first day and it wasnt until the second day when the housekeeper cleaned my room and it went away. I feel like where the hotel is located is awesome and great amenties however the maintenance in the hotel, hallway, walls, doors in rooms, cabinets were absolutely awful. so i would definitely say to renovate the rooms and carpet, walls in hallways.
Reviewed on Aug 18, 2026
Pittsville Hotel Deals
Princess Royale Oceanfront Resort
Oceanfront on 91st Street Ocean City MD
$151 nightly
$167 total
Sep 7 - Sep 8
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
$149 nightly
$167 total
Sep 13 - Sep 14
Total with taxes and fees
9/10 Wonderful! (3,802 reviews)
"The hotel was great and had a lot of things to do and we really enjoyed the bar and the karaoke."
Reviewed on Aug 18, 2026
Fenwick Inn
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
$93 nightly
$105 total
Sep 14 - Sep 15
Total with taxes and fees
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 Pittsville Vacation Packages
Pittsville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Salisbury - Ocean City Wicomico Regional Airport (SBY) |
Population | 1,450 |
Top Sights | Salisbury Zoo, Ward Museum of Wildfowl Art and Eastern Shore Baseball Hall of Fame Museum |
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Frequently asked questions
How much does a Pittsville vacation package cost?
You can grab a vacation package to this top destination from $1,229 on Expedia. But how much your vacation to Pittsville costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Pittsville?
You can usually find lower prices and greater availability in January, October and December. Browse our cheap Pittsville vacation packages and you could score some great off-season deals.
How many days is enough for Pittsville?
Generally, a handful of days is enough to go to the major sights during your Pittsville vacation. However, if you'd like to have time to rest or take day trips, think about extending your trip.
How to find the best Pittsville package deals?
Finding a cheap Pittsville package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Pittsville package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsville vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Pittsville vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Pittsville?
If you're considering a spontaneous Pittsville vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Pittsville vacation packages?
Your Pittsville break should be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs 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.
