Hillsmere Shores Vacation Packages

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Your Hillsmere Shores Vacation

Take the hard work out of travel planning with a Hillsmere Shores vacation package. A great neighborhood to stay in this captivating city is Historic District, which is good for history and a lot more. Ready to explore your new surroundings? U.S. Naval Academy, Maryland State House and William Paca House are just a few of the most popular places to visit during your trip to Hillsmere Shores. Expedia will help you escape your daily routine. Tailor your vacation to Hillsmere Shores to match your travel style, whatever that may be.

Top Hillsmere Shores Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.2/10 Very Good! (1,004 reviews)
First of all let me note that this is an "older" Hilton/Hampton Inn property...and it needs some updating. HOWEVER, the staff was over the top helpful and accommodating...they did EVERYTHING to make our stay so enjoyable...the morning breakfast team did an awesome job with service! The location is excellent, and only 5-15 minutes form Historic Annaoplis Maryland and other area attractions and restaurants. This Hampton Inn is a awesome value and I plan on staying there again when visiting family there in the Annapolis area!

Reviewed on Jul. 15, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9/10 Wonderful! (1,795 reviews)
Great location close to bars, restaurants a s shops.

Reviewed on Jul. 16, 2025

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
7.8/10 Good! (1,003 reviews)
Service was great. Hotel is beautiful. Good location from PG sports complex

Reviewed on Jun. 29, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Aug 30 - Sep 3
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Hotel was a little dirty

Reviewed on Jul. 13, 2025

Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

2 out of 5
North Laurel
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
7/10 Good! (1,011 reviews)
Thank you so much 🙏😍♥️

Reviewed on Jul. 14, 2025

Ready to book your vacation to Hillsmere Shores?

 

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Hillsmere Shores Hotel Deals

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 CA $140 per night from Jul 27 to Jul 28
CA $140
CA $206 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,789 reviews)
"Great location close to bars, restaurants a s shops."

Reviewed on Jul. 16, 2025

Historic Inns of Annapolis
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 CA $122 per night from Aug 17 to Aug 18
CA $122
CA $138 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (111 reviews)
"Great front desk staff!"

Reviewed on Jul. 14, 2025

Comfort Inn Largo-Washington DC East
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 CA $212 per night from Aug 3 to Aug 4
CA $212
CA $242 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,012 reviews)
"Great stay! Would come here again."

Reviewed on Jul. 14, 2025

Graduate by Hilton Annapolis
See all 1,260 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Hillsmere Shores

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

U.S. Naval Academy

4.5/5(8 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
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4.5/5(2 reviews)

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

What to do in Hillsmere Shores

Food Tour Plate

Historic Annapolis Food Tour

CA $109
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

CA $13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Annapolis: Pirates, Patriots, and Poltergeists of Old Town

CA $49
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 vacation package cost?
You'll find cheap prices from CA $264 on Expedia for your Hillsmere Shores break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Hillsmere Shores costs.
What are the cheapest months to go to Hillsmere Shores?
January, February and March are great times to search for cheap Hillsmere Shores vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Hillsmere Shores?
Allow at least 2 days for your Hillsmere Shores vacation if you're hoping to immerse yourself in all that makes this destination unique. Stroll around popular areas, including Parole and Historic District. Then check out top sights such as Westfield Annapolis Mall and Maryland Quiet Waters Park. With a well-planned itinerary, you'll be kept busy with room for some me-time too. Want to travel outside of Hillsmere Shores? Consider squeezing in an excursion or two.
How to find the best Hillsmere Shores package deals?
Bagging a cheap Hillsmere Shores package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Hillsmere Shores package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillsmere Shores vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can tailor your Hillsmere Shores getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Hillsmere Shores?
If you've got your Hillsmere Shores travel dates confirmed, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Hillsmere Shores?

  1. Choose when to go: Check your diary and get packing. Your favourite season and the activities available will also help you decide when to vacation in Hillsmere Shores.
  2. Plan your budget wisely: As well as the price of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Hillsmere Shores.
  3. Decide your trip length: Consider how long you'd like to spend exploring Hillsmere Shores. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now 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.