Highland Beach Vacation Packages
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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.
Top Highland Beach Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
Northeast
CA $615
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,006 reviews)
Great staff. Nice rooms. Free diffused ice water. Know that this hotel is on the Gallaudet campus, a deaf university. Has a shuttle to Union station. Plan your excursions on that time. The nearest metro stop is an easy 15 minute walk as an alternative
Reviewed on Aug 15, 2026
Ready to book your vacation to Highland Beach?
Highland Beach Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $135
CA $154 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,098 reviews)
"This is our favorite hotel to stay in while in the Annapolis area. The hotel is clean inside and out. Staff are so wonderful and genuinely care about your happiness. And a price point that trumps other hotels by far. We've stayed at another hotel that is right beside this one and were very disappointed, ..."
Reviewed on Aug 16, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
CA $127
CA $193 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,942 reviews)
"Unique and historic hotel with quaint rooms and well decorated period common spaces. Friendly staff and very clean."
Reviewed on Aug 16, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $143
CA $163 total
Sep 15 - Sep 16
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Very clean and classy place."
Reviewed on Aug 16, 2026
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: Historical Treasures of the City with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Best of Annapolis Tour: Colonial, State House, Naval Academy
CA $48
per adult
Frequently asked questions
How much does a Highland Beach vacation package cost?
You can grab a vacation package to this destination from CA $615 on Expedia. But how much your vacation to Highland Beach costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Highland Beach?
If you'd like to score a cheap Highland Beach vacation package, consider visiting in January, February and March. You'll generally find lower prices on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Highland Beach?
We recommend booking a Highland Beach vacation for at least 2 days. This gives you plenty of time to visit top sights including Westfield Annapolis Mall and Maryland Quiet Waters Park, as well as explore neighbourhoods like Parole and Historic District. You could even fit in a day trip beyond Highland Beach.
How to find the best Highland Beach package deals?
Begin your search for a Highland Beach package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Highland Beach package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Highland Beach escape underway.
Is it cheaper to book a Highland Beach vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Highland Beach vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Highland Beach?
Score incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Highland Beach trip.
How to plan a trip to Highland Beach?
- Choose when to go: Check your calendar and pack your bags. Your favourite time of year and the activities on offer will also help you decide when to visit Highland Beach.
- Set a budget: Consider costs like flights, meals and transportation when working out how much to put aside for your trip to Highland Beach. Then, choose a property that fits your budget, whether that's a low-cost stay or a more luxurious getaway.
- Decide how long to go for: Now that you're more familiar with Highland Beach, you can figure out the right length of your break. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
- Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Highland Beach vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
