Highland Beach Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Highland Beach

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
8.8/10 Excellent! (1,832 reviews)
Great Location Near Naval Academy and Shops/Dining
"Wonderful historic hotel with clean rooms and friendly staff. Close to Naval Academy and waterfront shops and dining (5-minute walk, tops). Also close to Maryland State House (across the street) and several other historical sites. Loved our stay, with many future stays planned as we visit our new ..."

Reviewed on 11 Aug 2025

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Historic Inns of Annapolis
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 4.222.203 ₫ per night from 2 Sept to 3 Sept
4.222.203 ₫
4.813.311 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Beautiful hotel in a great location!"

Reviewed on 10 Aug 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is 2.546.726 ₫ per night from 20 Aug to 21 Aug
2.546.726 ₫
2.903.268 ₫ total
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Nice place to stay...
"Nice place to stay when visiting Annapolis! Cost-effective, clean, a "want to assist" staff and close to Main Street and The Dock! Could not have selected a better place for a weekend stay with friends!"

Reviewed on 12 Aug 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,214 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.

Popular places to visit

Sandy Point State Park

Sandy Point State Park

Enjoy a trip to Sandy Point State Park and popular activities such as boating in Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Sandy Point State Park
Maryland State House showing heritage architecture and an administrative building

Maryland State House

After visiting Maryland State House, make a plan to see the other sights and activities in Annapolis. While you're in the area, stroll along the waterfront.

Maryland State House

Annapolis City Dock

You can enjoy retail therapy at Annapolis City Dock during your trip to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Annapolis City Dock

Frequently asked questions

How much does a Highland Beach holiday package cost?
You'll find cheap prices on Expedia for your Highland Beach escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Highland Beach costs.
What are the cheapest months to go to Highland Beach?
You can typically find lower prices and better availability in January, February and March. Explore our cheap Highland Beach holiday packages and you could land some excellent off-season deals.
How many days is enough for Highland Beach?
The ideal duration for your Highland Beach holiday depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Highland Beach package deals?
Use Expedia's handy filters to help you find some tempting Highland Beach package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Highland Beach package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Highland Beach holiday as a package?
You can enjoy significant savings on your next Highland Beach retreat by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Highland Beach?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Highland Beach break.
How to plan a trip to Highland Beach?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Highland Beach.
  2. Set a budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Highland Beach. Then, select a property that matches your budget, whether that's an economical option or a lavish getaway.
  3. Decide your trip length: Think about how long you want to spend exploring Highland Beach. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, lock in the right Highland Beach holiday package for you.