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.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was CA $912, price is now CA $665 per person
CA $665
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
Convenient location and spacious rooms
Reviewed on Jun 3, 2026
Salamander Washington DC
Southwest
Price was CA $1,851, price is now CA $1,160 per person
CA $1,160
per person
Aug 17 - Aug 21
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,094 reviews)
You are treated very well and see where your money goes!
Reviewed on Jun 1, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,979, price is now CA $1,288 per person
CA $1,288
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,192 reviews)
Our entire experience at the hotel was great and their staff was top notch.
Reviewed on Jun 2, 2026
The River Inn
Northwest
Price was CA $1,030, price is now CA $730 per person
CA $730
per person
Aug 17 - Aug 21
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,959 reviews)
Wonderful stay. Clean with amazingly friendly and helpful staff. Valet parking was seamless for arrivals and departures. The restaurant on site was great. We would definitely stay again.
Reviewed on Jun 2, 2026
Highland Beach Hotel Deals
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jun 16 to Jun 17
CA $155
CA $224 total
Jun 16 - Jun 17
includes taxes & fees
9/10 Wonderful! (1,858 reviews)
"Lovely hotel. Clean rooms, friendly staff. Highly recommend"
Reviewed on Jun 2, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $328 per night from Jun 15 to Jun 16
CA $328
CA $374 total
Jun 15 - Jun 16
includes taxes & fees
8.8/10 Excellent! (935 reviews)
"The room was incredibly small."
Reviewed on Jun 2, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jun 7 to Jun 8
CA $140
CA $159 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"It would have been a nicer stay if they weren’t ripping up flooring and had the awful headache causing smell of epoxy everywhere. The hotel room we were in was in another wing- and you had to pass all around the convention rooms to get there. Thankfully we were able to use the shuttle to go into ..."
Reviewed on Jun 2, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
