Highland Beach Vacations from $173

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Your Highland Beach Vacation

Planning your next adventure is a walk in the park with a Highland Beach vacation package. The neighborhood of Historic District, which is good for history, makes a terrific base to discover the delights of this unique city. Fill up your itinerary with tours of U.S. Naval Academy, Maryland State House and William Paca House, some of the top attractions you really should see during your trip to Highland Beach. Whatever your travel plans or budget, putting together a tailored Highland Beach vacation is a piece of cake with Expedia.

The Latest Highland Beach vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was $245, price is now $173 per person
$173
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,294 reviews)
Front desk help was great! Very nice hotel and room.

Reviewed on Oct 28, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Price was $272, price is now $191 per person
$191
per person
Dec 12 - Dec 14
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
8.2/10 Very Good! (1,016 reviews)
I got delayed and reached the hotel around 2am, yet I was able to get my room. I wasn't aware that breakfast was available or included, no mention.

Reviewed on Oct 22, 2025

Kent Island Resort

Kent Island Resort

3.5 out of 5
Save 100% on your flight
Price was $798, price is now $561 per person
$561
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
9.2/10 Wonderful! (114 reviews)
Walls and floors do not have any sound proofing, so we could hear guests above us walking back and forth until midnight. Then they resumed at 4:00 am for an hour before dragging luggage out. We were very tired the next day!

Reviewed on Oct 26, 2025

Metro Points Hotel

Metro Points Hotel

3 out of 5
Price was $284, price is now $204 per person
$204
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
7.4/10 Good! (1,401 reviews)
Parking area and workplaces were safe.

Reviewed on Oct 20, 2025

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Save 100% on your flight
Price was $488, price is now $351 per person
$351
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
8.6/10 Excellent! (2,410 reviews)
Great staff and vibes

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Highland Beach

U.S. Naval Academy which includes military items, interior views and heritage architecture

U.S. Naval Academy

4.5/5(446 reviews)

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4/5(270 reviews)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

4.5/5(13 reviews)

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

What to do in Highland Beach

Costa Rica Rainforest Guided Tram Tour

AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó

$67
per adult
AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

$26
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

$40
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Highland Beach

Highland Beach Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
$145 nightly
The price is $166 total per night from Nov 9 to Nov 10
$166 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,866 reviews)
All was very good except: no soap at sink in bathroom and none could be “found.” There was a coffee pot that had to be replaced with one that could work with the type coffee pods provided. Promptly replaced, but how could housekeeping have an outdated coffee maker for older-type coffee filter ...

Reviewed on Oct 28, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $169 total per night from Nov 24 to Nov 25
$169 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,019 reviews)
Front desk staff friendly. But there attire is not very appropriate

Reviewed on Oct 26, 2025

Graduate by Hilton Annapolis
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
$97 nightly
The price is $110 total per night from Nov 18 to Nov 19
$110 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Country Inn and Suites, Annapolis MD
The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it.

Reviewed on Oct 27, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,229 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.

Find the Best Highland Beach Vacation Packages

Highland Beach Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Top Sights
Sandy Point State Park, Sandy Point Beach and Bay Ridge Beach

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Frequently asked questions

How much does a Highland Beach vacation package cost?
You'll find cheap prices from $173 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 rates and greater availability in January, October and December. Browse our cheap Highland Beach vacation packages and you could score some great off-season discounts.
How many days is enough for Highland Beach?
The ideal length of your Highland Beach vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to hit all the major sights and explore 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.
Does Expedia offer Book Now, Pay Later Highland Beach vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Highland Beach vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.