Hillsmere Shores Vacations

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Find the Best Hillsmere Shores Vacation Packages

Hillsmere Shores Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
The price is ₩141,009 per night from Sep 8 to Sep 9
₩141,009
₩208,068 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,828 reviews)
"Fantastic!"

Reviewed on Aug 25, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
The price is ₩222,272 per night from Sep 2 to Sep 3
₩222,272
₩253,391 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Very good"

Reviewed on Aug 20, 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
The price is ₩139,949 per night from Sep 1 to Sep 2
₩139,949
₩159,542 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Great"

Reviewed on Aug 24, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,276 properties in Hillsmere Shores
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.

Discover the most popular places to visit in Hillsmere Shores

U.S. Naval Academy which includes military items, interior views and heritage architecture

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
Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters Park

Frequently asked questions

How much does a Hillsmere Shores vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Hillsmere Shores costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Hillsmere Shores?
If you'd like to snag a cheap Hillsmere Shores vacation package, consider traveling in January, February and March. You'll typically find lower prices on flights and accommodations during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Hillsmere Shores?
With a well-organized schedule, you can easily tick off the top Hillsmere Shores attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your Hillsmere Shores vacation for longer.
How to find the best Hillsmere Shores package deals?
Start your search for a Hillsmere Shores package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Hillsmere Shores package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillsmere Shores adventure off to a flying start.
Is it cheaper to book a Hillsmere Shores vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. 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 flexibility to create a tailored Hillsmere Shores vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Hillsmere Shores?
If you've got your Hillsmere Shores travel dates confirmed, book as soon as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Hillsmere Shores?

  1. Pick your dates: The things you'd like to do in Hillsmere Shores and your favorite season will help you decide when to go.
  2. Set your budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Hillsmere Shores. Then, pick a hotel that fits your budget, whether that's an affordable stay or a high-end getaway.
  3. Decide how long to go for: Now that you're more familiar with Hillsmere Shores, you can figure out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Hillsmere Shores vacation package that brings all your bookings together.

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