Pittsville Vacations

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Find the Best Pittsville Vacation Packages

Pittsville Hotel Deals

Grand Hotel Ocean City Oceanfront
Grand Hotel Ocean City Oceanfront
3 out of 5
2100 N Baltimore Ave, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AED 328 per night from Jun 8 to Jun 9
AED 328
AED 422 total
8 Jun - 9 Jun
includes taxes & fees
9/10 Wonderful! (2,843 reviews)
"Wonderful and helpful staff."

Reviewed on 5 June 2025

Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort
Princess Royale Oceanfront Resort
3 out of 5
Oceanfront on 91st Street, Ocean City, MD
8.2/10 Very Good! (1,890 reviews)
"I scheduled a getaway for my mother’s 66th birthday here and the trip itself was great. Unfortunately I had requested a fruit basket to be setup in the hotel room upon arrival and it wasn’t. It came the next day and was old nasty fruit & cheese. We loved our room and the cleanliness of the hotel. ..."

Reviewed on 5 June 2025

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Princess Royale Oceanfront Resort
Fenwick Inn
Fenwick Inn
3 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AED 1,088 per night from Jun 20 to Jun 21
AED 1,088
AED 1,262 total
20 Jun - 21 Jun
includes taxes & fees
8.6/10 Excellent! (1,955 reviews)
"This hotel has THE BEST POOL, HOT TUB, and SPLASH area in OCEAN CITY!!! The pool is always warm. The rooms are spacious and clean. The view and breakfast were nice. The staff is always friendly and we have no problem getting any extra items we may need. The beds are comfortable and it's a safe, relaxing ..."

Reviewed on 4 June 2025

Fenwick Inn
See all 9,208 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 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.