Highland Beach 2024 Holidays

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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
The price is €146 per night from 10 Jul to 11 Jul
€146
per night
10 Jul - 11 Jul
8.8/10 Excellent! (1,606 reviews)
"I can’t say enough good things about this Inn. Location, staff, cleanliness, and amenities were all of a 5 star, first class Inn at Expedia prices. Highly recommend!"

Reviewed on 24 Jun 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is €198 per night from 1 Jul to 2 Jul
€198
per night
1 Jul - 2 Jul
9.2/10 Wonderful! (1,023 reviews)
"Second visit in 2 weeks, just as great as first."

Reviewed on 21 Jun 2024

Graduate Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is €255 per night from 7 Jul to 8 Jul
€255
per night
7 Jul - 8 Jul
8.8/10 Excellent! (728 reviews)
"Overall fantastic location! Within easy walking distance of shops & dining and a quick $4 water taxi ride that runs all day to get to the other side of the harbor. Rooms are quaint, well appointed. A bit pricey but the location makes up for it. Valet parking only but very reasonable."

Reviewed on 24 Jun 2024

Annapolis Waterfront Hotel, Autograph Collection
See all 1,119 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.

Frequently asked questions

How much does a Highland Beach holiday package cost?
Tailor make your Highland Beach package from just . Pick from any combination of rental cars, flights and hotels to put together the escape you’ve been dreaming about for ages. Be sure to add on a few experiences or activities!
How do I get a cheap travel package to Highland Beach?
Browse and book everything in one place with our Highland Beach holiday packages. You’ll find bargains on flights, hotels and more that’ll keep your travel budget happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 hotel options globally to select from, there are endless opportunities to mix and match as you please.
Where should I stay in Highland Beach?
Most visitors to Highland Beach include U.S. Naval Academy and Maryland State House on their itineraries. Why not go for a hotel right near these popular attractions?
How far in advance should I book my Highland Beach holiday?
Get rewarded with the biggest variety at the cheapest prices by booking your holiday to Highland Beach early. Air carriers usually advertise flights anywhere up to 12 months in advance, so secure your spot ASAP. That said, Expedia is dedicated to giving you the best deals around, so it’s never a bad time to book your dream holiday!
What does an Expedia Highland Beach travel package include?
Expedia has all you need to book your Highland Beach trip, but how your package is structured is totally up to you. Pick from a combination of hotels, flights and rental cars. After some tours or activities to keep you on the move? Once you’ve made your booking, you can add them on too. No matter your style, there’s a package deal to suit your needs.
What should I know before booking a Highland Beach travel package?
You’ll land great savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one place makes trip planning easier. So why waste your time or money? Whether you’re organising a ritzy city getaway or a budget solo adventure, have a look at our package deals today.
Can I choose my airline with a Highland Beach Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to pick from worldwide. With such a big range of choice, finding the perfect carrier to get you to Highland Beach will be a snap.
If I'm not able to travel, can I cancel my Highland Beach holiday package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Highland Beach holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.

Popular places to visit

Image for U.S. Naval Academy

U.S. Naval Academy

4.5/5(5 reviews)

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
Image for 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
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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

What to do in Highland Beach

Image for Phantoms of Annapolis Ghost Walking Tour

Phantoms of Annapolis Ghost Walking Tour

€30
Per adult
Phantoms of Annapolis Ghost Walking Tour
Image for Ghosts of Annapolis: Boos & Booze Haunted Pub Crawl

Ghosts of Annapolis: Boos & Booze Haunted Pub Crawl

€32
Per adult
Ghosts of Annapolis: Boos & Booze Haunted Pub Crawl
See all activities in Highland Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.