Pittsville Holidays

Book a Hotel + Flight or Car together to unlock savings

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! (2,018 reviews)
"It was clean and comfortable and had all of the things we needed. Enjoyed our stay very much"

Reviewed on 20 Aug 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 5.672.832 ₫ per night from 12 Sept to 13 Sept
5.672.832 ₫
6.691.119 ₫ total
12 Sept - 13 Sept
includes taxes & fees
8.6/10 Excellent! (1,939 reviews)
"The hotel is very nice, the rooftop bar is great, rooms modern. However they have a hard check-in that everyone has to check in at 4:00. We waited 40 minutes to check in and there were still vacationers in line. At 3:00 we were told for an extra $100 early check in was available. Stupid policy needs ..."

Reviewed on 20 Aug 2025

Fenwick Inn
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
9/10 Wonderful! (3,117 reviews)
"The trip was a bust because weather was bad. The hotel was nice and clean."

Reviewed on 20 Aug 2025

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Grand Hotel Ocean City Oceanfront
See all 9,338 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 holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday 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 holiday 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 holiday 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," "Traveller 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsville holiday as a package?
Expedia holiday 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 customised Pittsville holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Pittsville?
If you're considering a spontaneous Pittsville holiday, 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 accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Pittsville holiday package for you.