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.
Hotel Nell - Union Market

Hotel Nell - Union Market

4 out of 5
Northeast
Price was CA $642, price is now CA $492 per person
CA $492
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.6/10 Excellent! (1,388 reviews)

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Price was CA $2,737, price is now CA $1,918 per person
CA $1,918
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,128 reviews)

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was CA $1,327, price is now CA $992 per person
CA $992
per person
Sep 24 - Sep 27
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,423 reviews)
Great hotel!

Reviewed on Jul 23, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $1,012, price is now CA $792 per person
CA $792
per person
Sep 25 - Sep 27
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (2,971 reviews)
Great location. Easy walk to both the inner harbour and Camden yards.

Reviewed on Jul 24, 2026

The Ritz-Carlton, Tysons Corner

The Ritz-Carlton, Tysons Corner

5 out of 5
Tysons
Price was CA $1,606, price is now CA $1,263 per person
CA $1,263
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,006 reviews)
Very nice and great location

Reviewed on Jul 22, 2026

Ready to book your vacation to Highland Beach?

 

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Highland Beach Hotel Deals

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 23 to Aug 24
CA $144
CA $165 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (1,055 reviews)
"Beautiful area. Beautiful room. Small icebox. Good water pressure. Smelled great. Room didn't get cold enough for us but it was comfortable! The beds was decent. A little hard for us but still nice. Overall it was a great stay and we would stay again. 😊"

Reviewed on Jul 24, 2026

DoubleTree by Hilton Hotel Annapolis
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
The price is CA $150 per night from Aug 10 to Aug 11
CA $150
CA $219 total
Aug 10 - Aug 11
includes taxes & fees
Historic Inns of Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Aug 18 to Aug 19
CA $115
CA $127 total
Aug 18 - Aug 19
includes taxes & fees
St Michaels Inn
See all 1,209 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.
All Inclusive Vacations
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Beach Vacations
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What to do in Highland Beach

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $14
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $45
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

CA $51
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
See all activities in Highland Beach

Frequently asked questions

How much does a Highland Beach vacation package cost?
You can grab a vacation package to this destination from CA $492 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.