Highland Beach Trips (flight + hotel)

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    Save up to P 3,118 when you book a flight and hotel together*
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    Plan, book, and manage your trip all in one place

Top hotels in Highland Beach

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,792 reviews)
"Close to shops, restaurants , water front, and nightlife"

Reviewed on Jun 23, 2025

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Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is P5,807 per night from Jul 21 to Jul 22
P5,807
P6,620 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"It was very nice and comfortable"

Reviewed on Jun 22, 2025

Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is P5,725 per night from Jul 28 to Jul 29
P5,725
P6,526 total
Jul 28 - Jul 29
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Loved my stay! There were some water stains on top of the room which I would guess is just cons of Maryland weather since I was on the top floor. But the breakfast was great, which is hard to find after Covid and the staff were so friendly and accommodating. Also the room itself was a classic style ..."

Reviewed on Jun 23, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,216 properties in Highland Beach
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 Highland Beach vacation package cost?
You'll find cheap prices on Expedia for your Highland Beach escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation 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 vacation 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 vacation 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 vacation package as soon as possible.
Is it cheaper to book a Highland Beach vacation as a package?
You can enjoy significant savings on your next Highland Beach retreat by booking a personalized vacation 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 vacation 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?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Highland Beach.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Highland Beach vacation package for you.

What to do in Highland Beach

Food Tour Plate

Historic Annapolis Food Tour

P4,494
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

P1,348
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

P1,685
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Highland Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.