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.
Hyatt Regency Washington on Capitol Hill
Northwest
CA $686
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,012 reviews)
Traveling as a family. Great location near Capitol Hill. Short walk to train station (2-3 blocks). Taxis in front of hotel as well as pay as you go scooters and bikes.
Reviewed on Oct 17, 2026
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
CA $1,165
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,226 reviews)
This is a beautiful property in a great location. All the staff from the concierge, doorman, and front desk were all friendly and welcoming. We had a great stay. We come to DC often and decided based on this visit this is our new go to place.
Reviewed on Oct 15, 2026
Ready to book your vacation to Highland Beach?
Highland Beach Hotel Deals
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
CA $208
CA $237 total
Oct 26 - Oct 27
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Clean room, very nice decor and great staff"
Reviewed on Oct 16, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $157
CA $178 total
Oct 20 - Oct 21
includes taxes & fees
8.8/10 Excellent! (1,245 reviews)
"The staff are very nice. The room was clean but the hotel itself looked dirty and"
Reviewed on Oct 16, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
CA $186
CA $207 total
Oct 27 - Oct 28
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. ..."
Reviewed on Oct 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: Annapolis Harbor and U.S. Naval Academy Cruise
CA $48
per adult
90% of travellers recommend
Annapolis Harbor and U.S. Naval Academy Cruise
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 $686 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.
