Hillsmere Shores Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Hillsmere Shores

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
8.8/10 Excellent! (1,831 reviews)
"The location was wonderful. The hotel is quaint and a lovely place to stay. I only interacted with the front desk staff but she was very kind. I’m excited to come back."

Reviewed on 17 Aug 2025

Get rates
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
The price is 4.223.810 ₫ per night from 2 Sept to 3 Sept
4.223.810 ₫
4.815.143 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"Great location and fun hotel theme! Very nice staff. Walked to shops and food - loved Boatyard Restaurant. Thank you!"

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 2.549.730 ₫ per night from 26 Aug to 27 Aug
2.549.730 ₫
2.906.693 ₫ total
26 Aug - 27 Aug
includes taxes & fees
9/10 Wonderful! (1,012 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

Sandy Point State Park

Sandy Point State Park

Enjoy a trip to Sandy Point State Park and popular activities such as boating in Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Sandy Point State Park
Maryland State House showing heritage architecture and an administrative building

Maryland State House

After visiting Maryland State House, make a plan to see the other sights and activities in Annapolis. While you're in the area, stroll along the waterfront.

Maryland State House

Annapolis City Dock

You can enjoy retail therapy at Annapolis City Dock during your trip to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Annapolis City Dock

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.