Hillsmere Shores Holidays

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Top hotels in Hillsmere Shores

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! (1,835 reviews)
"Customer service was A++. Great fromt desk staff and the coffee bar in the morning was really good!"

Reviewed on 18 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 €157 per night from 2 Sept to 3 Sept
€157
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Cool place, comfy bed!!!
"Cool place, cool vibe! Loved all the pictures and the strong decor. Front desk check in and out was quick & efficient. The parking valets were quick and very friendly. Walking distance to shopping, restaurants and bars! The bed was super comfy! We would definitely stay here again!"

Reviewed on 20 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 €95 per night from 27 Aug to 28 Aug
€95
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"It was good."

Reviewed on 19 Aug 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.

Popular places to visit

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
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
Maryland State House showing an administrative building and heritage architecture

Maryland State House

Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.

Maryland State House

What to do in Hillsmere Shores

Food Tour Plate

Historic Annapolis Food Tour

€69
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

€8
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Pirates, Patriots, and Poltergeists of Old Town

Annapolis: Pirates, Patriots, and Poltergeists of Old Town

€23
per adult
Annapolis: Pirates, Patriots, and Poltergeists of Old Town
See all activities in Hillsmere Shores

Frequently asked questions

How much does a Hillsmere Shores holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday package, consider travelling in January, February and March. You'll typically find lower prices on flights and accommodation during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Hillsmere Shores?
With a well-organised 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 holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 favourite 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 holiday 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.