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.
The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was CA $749, price is now CA $532 per person
CA $532
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,009 reviews)
I would highly recommend this hotel to anyone. The staff are nice and helpful when we had questions. The staff at Root &Vine when we order pizza's to take back to our room. The sercurity guards in the lobby would always say hi and ask how you are doing. The room was amazing and we enjoyed the view from our room.

Reviewed on Apr 10, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,173, price is now CA $1,548 per person
CA $1,548
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.8/10 Exceptional! (59 reviews)
We absolutely loved staying at this hotel. The room was clean, comfortable, and the decor was awesome. The hotel staff was very friendly and accommodating. The location is great, walking distance to cute coffee shops, restaurants, and shops. Overall, loved our stay!

Reviewed on Mar 22, 2026

Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Price was CA $1,419, price is now CA $1,062 per person
CA $1,062
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
Everything was amazing the only issue I had was Expedia over booked. Karen was such a help on the matter. She was friendly, patient, & accommodating. She helped to make my trip amazing so grateful for her!

Reviewed on Apr 16, 2026

Elegant 2BR Apartment - Minutes to D.C.

Elegant 2BR Apartment - Minutes to D.C.

3.5 out of 5
Crystal City
Price was CA $1,944, price is now CA $1,489 per person
CA $1,489
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.8/10 Exceptional! (7 reviews)
Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $776, price is now CA $596 per person
CA $596
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (743 reviews)
Great spot. Will return.

Reviewed on Apr 16, 2026

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Highland Beach Hotel Deals

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 3 to May 4
CA $247
CA $281 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Outstanding

Reviewed on Apr 11, 2026

Graduate by Hilton 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 $208 per night from May 17 to May 18
CA $208
CA $284 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,846 reviews)
I parked at the public garage close by and reasonably priced.

Reviewed on Apr 17, 2026

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 3 to May 4
CA $175
CA $200 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Friendly, excellent service, very clean, and great location (very close to downtown.

Reviewed on Apr 14, 2026

Hilton Garden Inn Annapolis Downtown
See all 1,208 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.
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Discover the most popular places to visit in Highland Beach

U.S. Naval Academy

U.S. Naval Academy

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

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 $13
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 $49
per adult
Ashes and Apparitions of Annapolis Ghost Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $41
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Highland Beach

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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.