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.
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Price was CA $976, price is now CA $732 per person
CA $732
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (2,363 reviews)
The food was great, The room was greatly sized. But the closet in the room had a moldy smell. Which over came the room.

Reviewed on Jun 30, 2026

Entire House 1BD King Bed near Downtown

Entire House 1BD King Bed near Downtown

3 out of 5
Hollins Market
Price was CA $1,356, price is now CA $1,013 per person
CA $1,013
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (13 reviews)
Had to contact host.she first said I didn't have a reservation then asked for a copy of my id. Ridiculous!

Reviewed on Jun 14, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $1,392, price is now CA $1,040 per person
CA $1,040
per person
Sep 5 - Sep 9
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9/10 Wonderful! (1,203 reviews)
Every staff member we interacted with seemed completely disinterested in the guests. The woman at the front desk put us in one of the absolute worst rooms and didn’t explain how to reach the room which was on the second floor behind some doors that looked like big brown swinging kitchen doors. My husband and I were celebrating our 30th anniversary and wanted to go someplace special - we were so disappointed in the Sofitel DC experience. We will never go there again!

Reviewed on Jun 28, 2026

The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel

3 out of 5
Fells Point
Price was CA $2,172, price is now CA $1,625 per person
CA $1,625
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
9.2/10 Wonderful! (818 reviews)
Great to see Eric and the crew again! Always a great stay here! We’ll be back!

Reviewed on Jun 29, 2026

Motel 6 Laurel, DC - Washington Northeast

Motel 6 Laurel, DC - Washington Northeast

2 out of 5
Maryland City
Price was CA $1,289, price is now CA $979 per person
CA $979
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
7.8/10 Good! (1,780 reviews)
I made a mistake putting my name on the reservation wrong and nobody helped me so I lost my money

Reviewed on Jun 26, 2026

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Highland Beach Hotel Deals

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 $128 per night from Jul 15 to Jul 16
CA $128
CA $194 total
Jul 15 - Jul 16
includes taxes & fees
9/10 Wonderful! (1,877 reviews)
"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I ..."

Reviewed on Jun 29, 2026

Historic Inns of Annapolis
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 $135 per night from Jul 5 to Jul 6
CA $135
CA $154 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,022 reviews)
"Great spot to stay! Had the pleasure of checking in with Trendy- an amazingly refreshing soul that is passionate both about his job and customer satisfaction. I felt very welcomed and informed upon arrival- and he was key in making that happen. The property is worth more than what you pay. Spacious ..."

Reviewed on Jul 1, 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is CA $162 per night from Jul 26 to Jul 27
CA $162
CA $184 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"It wasn’t the property or the room.. It was the unfriendly staff members. Not a single smile from the second we walked in… the front desk act as if we were bothering them.. never again"

Reviewed on Jun 29, 2026

Crowne Plaza Annapolis by IHG
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.
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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
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $111
per adult
Historic Annapolis Food Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $44
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
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 $732 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.