Hillsmere Shores Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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! (1,789 reviews)
"Wonderful experience at a beautiful, historic hotel. Great location!"

Reviewed on 16 Jun, 2025

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Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 21 Jul to 22 Jul
S$158
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Conveniently located and clean. Great prices"

Reviewed on 19 Jun, 2025

Hilton Garden Inn Annapolis Downtown
Comfort Inn Largo-Washington DC East
Comfort Inn Largo-Washington DC East
3 out of 5
9421 Largo Drive West, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 8 Jul to 9 Jul
S$110
8 Jul - 9 Jul
includes taxes & fees
8/10 Very Good! (61 reviews)
"I found the hotel clean and very friendly. The bed was so comfortable. The hotel provided great customer service, especially at the front desk. I would definitely stay there again."

Reviewed on 12 Jun, 2025

Comfort Inn Largo-Washington DC East
See all 1,250 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.

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.

What to do in Hillsmere Shores

Food Tour Plate

Historic Annapolis Food Tour

S$103
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

S$31
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

S$51
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Hillsmere Shores

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.