Highland Beach Holidays from £895
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Your Highland Beach Holiday
Planning your next adventure is a walk in the park with a Highland Beach holiday package. The neighbourhood 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 holiday is a piece of cake with Expedia.
Top Highland Beach Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Arlo Washington DC
Northwest
£895
per person
5 Jan - 9 Jan
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Baltimore (BWI)
9.4/10 Exceptional! (2,129 reviews)
my stay at the Arlo was extraordinarily easy ,comfortable, clean , modernized... the staff
are knowledgeable , friendly, happy amazing helpful!
Come be a part of it all!
Reviewed on 16 Oct 2026
One Washington Circle DC, Tapestry Collection by Hilton
Downtown Washington D.C.
£1,013
per person
12 Dec - 17 Dec
found 15 hours ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9.2/10 Wonderful! (1,003 reviews)
Had a great stay! Staff were very friendly! Rooms were very clean!
Reviewed on 15 Oct 2026
Highland Beach Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Sandy Point State Park, Sandy Point Beach and Bay Ridge Beach |
Top hotels in Highland Beach
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
£126
26 Oct - 27 Oct
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Clean room, very nice decor and great staff"
Reviewed on 16 Oct 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
£95
19 Oct - 20 Oct
includes taxes & fees
8.8/10 Excellent! (1,245 reviews)
"The staff are very nice. The room was clean but the hotel itself looked dirty and"
Reviewed on 16 Oct 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
£110
17 Nov - 18 Nov
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. ..."
Reviewed on 16 Oct 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.
What to do in Highland Beach
Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
£25
per adult
90% of travellers recommend
Annapolis Harbor and U.S. Naval Academy Cruise
£25
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
£7
per traveller
80% of travellers recommend
Frequently asked questions
How much does a Highland Beach travel package cost?
Perhaps less than you might think — from just £895, actually! By bundling hotels, flights and car rentals into a customized travel package, your Highland Beach escape is only clicks away.
If I'm not able to travel, can I cancel my Highland Beach travel package?
Yes, you can. We understand that life doesn't always go to plan, so we're here to help if you need to make changes to your Highland Beach travel package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Highland Beach?
Find flights that suit your schedule, add a hotel to your booking and watch the savings pile up with a Highland Beach holiday package. It's that easy! From flights and hotels to activities and rental cars, Expedia makes travelling on the cheap easy. And with more than 550 partner airlines and 1,000,000 hotel options throughout the world to choose from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Highland Beach holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Check out these flexible payment options:
- Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
- Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan from Klarna.
Where should I stay in Highland Beach?
A trip to Highland Beach isn't complete without stopping by U.S. Naval Academy and Maryland State House. Stay at a hotel right nearby so you can easily access these terrific tourist attractions.
What are the top hotels in Highland Beach?
Graduate Annapolis and Historic Inns of Annapolis are two of the most popular properties in Highland Beach. Why not have a look at the amenities and rates at each and then make up your mind?
How far in advance should I book my Highland Beach holiday?
Reward yourself with the biggest variety and the lowest prices by booking your holiday to Highland Beach early. Airlines usually sell tickets anywhere up to 12 months before departure, so start locking things in as soon as you can. That being said, Expedia is committed to providing you with the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Highland Beach travel package include?
From hotels and airfares to rental cars, Expedia can help you shape a Highland Beach package that suits you. Holidaying for a while? Check out a flight, rental car and hotel bundle. If you can only manage a quick getaway, a flight and hotel deal could be what you're after. Experiences can also be added once you've made your booking. Our travel packages make it a cinch to save and plan.
What should I know before booking a Highland Beach travel package?
Find deals to suit your budget with an Expedia package. Airfares, hotels, rental cars — we've got all of them. You'll save precious dollars just by bundling your bookings. Whether you're going on a skiing adventure or drinking cocktails on a beach, your dream getaway is just a few clicks away.
Can I choose my airline with a Highland Beach Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to select from around the globe. With so much choice, finding the ideal carrier to get you to Highland Beach won't be difficult.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
