Pittsville Trips (flight + hotel)

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Top hotels in Pittsville

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
8.4/10 Very Good! (1,966 reviews)
"The property was cleanly renovated and very upscale in appearance. Plenty of amenities right on the beach. We will be booking again next year."

Reviewed on Aug 5, 2025

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Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave, Ocean City, MD
9/10 Wonderful! (3,054 reviews)
"My family and I had a wonderful stay. We even decided to extended our trip. The hotel was very accommodating with our request to stay longer. We will definitely return in the future!"

Reviewed on Aug 4, 2025

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Grand Hotel Ocean City Oceanfront
Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is P11,881 per night from Aug 29 to Aug 30
P11,881
P14,050 total
Aug 29 - Aug 30
includes taxes & fees
8.6/10 Excellent! (1,980 reviews)
"The new and improved Fenwick inn did a nice job with the room upgrades. Room was spacious and clean and bright! Comfortable king size bed. Nice roof top bar and restaurant. We did not get a chance to use the indoor pool which was crowded with adults and kids. Breakfast was hit or miss but adequate. ..."

Reviewed on Aug 3, 2025

Fenwick Inn
See all 9,346 properties in Pittsville
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 Pittsville vacation package cost?
You can grab a vacation package to this top destination 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?
Travel in the low or shoulder season and you're likely to get cheap Pittsville vacation packages. Remember that public holidays and major local events can have an impact on prices, so do some research before you go.
How many days is enough for Pittsville?
With a well-planned schedule, you can easily hit the main Pittsville attractions in a few days. But if you prefer to discover hidden gems or go on day trips, think about booking your Pittsville vacation for longer.
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.
How to plan a trip to Pittsville?

  1. Pick your travel dates: The things you plan to do in Pittsville and your preferred season will help you decide when to go.
  2. Set a budget: Factor in costs like flights, transportation and food when calculating how much to set aside for your trip to Pittsville. Then, choose a hotel that matches your budget, whether that's an economical stay or a more upscale getaway.
  3. Work out your trip length: Consider how much time you want to spend discovering Pittsville. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Pittsville vacation package for you.

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