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.
Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,681, price is now CA $1,123 per person
CA $1,123
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,006 reviews)
It was ok. I liked the aesthetic of the lobby. Couldn’t use the pool it was closed for renovations. The room was alright. Kinda small. I wouldn’t put more than 2 in there. The bed was comfy. The bathroom was small. It had a rain shower. I hate rain showers. The shower had no racks so I had to sit my stuff on the floor in the shower. Not much counter space The doors to the room and the bathroom are super heavy. The bathroom floor got really wet from the shower. But the water was nice and hot. I really liked the kitchenette area. It was a nice size mini fridge The breakfast was ok. I would stay here again.

Reviewed on Jun 29, 2026

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Price was CA $1,813, price is now CA $1,198 per person
CA $1,198
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,106 reviews)
My stay was everything I could have imagined. The staff were extremely friendly and attentive. Hospitality was 10 out of 10. The spa services were amazing. Would definitely stay here again.

Reviewed on Jul 2, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,903, price is now CA $1,287 per person
CA $1,287
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,000 reviews)
The Sheraton is in a great location, we were there for a family wedding and close to everything. Parking was very easy on site (for a fee). There was no breakfast included so we didn’t make it down to the restaurant but there is a very convenient Starbucks in the lobby. The only negative I would say is when you get off the elevator on the floor it felt very humid and hot bc there seemed to always be someone doing laundry. Highly recommend

Reviewed on Jul 2, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,758, price is now CA $1,228 per person
CA $1,228
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Rachael's Inner Harbor Boutique Inn

Rachael's Inner Harbor Boutique Inn

3 out of 5
Ridgely's Delight
Price was CA $2,244, price is now CA $1,572 per person
CA $1,572
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
10/10 Exceptional! (5 reviews)
I did not see shops per se. However, Camden yards was a short walk away.

Reviewed on Jun 27, 2026

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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 $128 per night from Jul 28 to Jul 29
CA $128
CA $194 total
Jul 28 - Jul 29
includes taxes & fees
9/10 Wonderful! (1,867 reviews)
"Staff was friendly, helpful and wonderful. Room was good, location is great."

Reviewed on Jul 3, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 5 to Jul 6
CA $135
CA $154 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"The room is clean. Spacious and quiet. Bed is comfortable. We will stay here again."

Reviewed on Jul 3, 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is CA $162 per night from Jul 12 to Jul 13
CA $162
CA $185 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Excelent"

Reviewed on Jul 2, 2026

Crowne Plaza Annapolis by IHG
See all 1,274 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.
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What to do in Hillsmere Shores

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

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

CA $14
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $111
per adult
Historic Annapolis Food Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $44
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
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 $1,123 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.

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