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.
Capitol Hill Hotel
Capitol Hill
CA $961
per person
Oct 31 - Nov 4
found 9 hours ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (1,405 reviews)
The television didn’t work and when I told the front desk, they just said that tell maintenance. So I paid for a hotel with a television and didn’t have a television. No offer of a discount nothing.
Reviewed on Sep 7, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
CA $2,130
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (1,249 reviews)
DO NOT PAY FOR BREAKFAST!!!!! I just stayed two nights at the Sofitel Hotel in Washington DC. Everything was perfect until breakfast time the following morning.
Both days we had to wait over half hour to be seated for breakfast. I almost lost my tour. Besides waiting for a long time. Food took another 20 minutes to arrive at our table. And another 10 minutes to get the check. Clearly they are under staff.
The second morning, the line for breakfast was longer. We needed to drive fours hours to go back home. So I went to the front desk and asked to be credited back for one day for our breakfast since we couldn't wait for over one hour and a half to have breakfast. They told me NO, the it was part of a package and I said, I selected the breakfast option. I paid more to have the breakfast, is not like the hotel includes the breakfast in your rate. The breakfast is a sit down breakfast, it is not a buffet. The manager said that he can only do a room service and that it was going to be faster. He said take it or leave it. He said if "you don't use it you loose it", What type of customer service is that. I saw a lot of people complaining. Some people left saying that they will dispute the charges.
The Hotel is in a perfect location, everything was clean. I have no other complain besides the breakfast taking a long time. Tourist usually have tours schedules and breakfast should not take this long. I am very disappointed at this hotel brand.
Reviewed on Sep 7, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
CA $1,630
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.4/10 Very good! (1,005 reviews)
The room had a good massage chair that worked well! The first day there was a fishy smell all across the property and the room smelled like it had been smoked in.
Reviewed on Sep 7, 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 $115
CA $131 total
Sep 27 - Sep 28
includes taxes & fees
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $152
CA $173 total
Sep 15 - Sep 16
includes taxes & fees
8.6/10 Excellent! (1,024 reviews)
"Great hotel! Wish the microwave was in the room."
Reviewed on Sep 6, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
CA $214
CA $244 total
Oct 1 - Oct 2
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"GREAT location! The room was huge & beautifully decorated. We are excited to come back again! 10/10!"
Reviewed on Sep 7, 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
Ashes and Apparitions of Annapolis Ghost Tour
CA $50
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
CA $42
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 $961 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.
