Highland Beach Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Highland Beach
Price found within the past 48 hours. Click for updated prices.
Top hotels in Highland Beach
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
€96
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,143 reviews)
"Super friendly front staff & cleaning ladies, also extremely easy to get everything booked and checked in/out!"
Reviewed on 30 Aug 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
€134
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,982 reviews)
"Location, cleanliness, price, friendliness of the staff. Love it there. Only place we stay when visiting Annapolis."
Reviewed on 30 Aug 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
€151
13 Sept - 14 Sept
includes taxes & 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.
What to do in Highland Beach
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
€26
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
€8
per traveller
80% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
€31
per adult
Frequently asked questions
How much does a Highland Beach holiday package cost?
You'll find cheap prices from €1,021 on Expedia for your Highland Beach escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Highland Beach costs.
What are the cheapest months to go to Highland Beach?
You can typically find lower prices and better availability in January, February and March. Explore our cheap Highland Beach holiday packages and you could land some excellent off-season deals.
How many days is enough for Highland Beach?
The ideal duration for your Highland Beach holiday depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Highland Beach package deals?
Use Expedia's handy filters to help you find some tempting Highland Beach package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Highland Beach package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Highland Beach holiday as a package?
You can enjoy significant savings on your next Highland Beach retreat by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Highland Beach?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Highland Beach break.
How to plan a trip to Highland Beach?
- Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Highland Beach.
- Set a budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Highland Beach. Then, select a property that matches your budget, whether that's an economical option or a lavish getaway.
- Decide your trip length: Think about how long you want to spend exploring Highland Beach. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
- Combine your airfare and accommodation: Once you've nailed down your dates and duration, lock in the right Highland Beach holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
