Hillsmere Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Hillsmere

Find the best Hillsmere areas and neighborhoods for the activities you enjoy most. Learn more about Hillsmere
Annapolis which includes a city and street scenes as well as a small group of people

Historic District

1 out of top 10 points of interest in this area

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State House.

Find hotels in Historic District

Top hotels in Hillsmere

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 S$111 per night from 4 Jan to 5 Jan
S$111
4 Jan - 5 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
Room was ok other than being in the basement, the staff was awesome and friendly

Reviewed on 20 Dec, 2025

DoubleTree by Hilton Hotel Annapolis
The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
7795 Arundel Mills Blvd Hanover MD
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 30 Dec to 31 Dec
S$158
30 Dec - 31 Dec
includes taxes & fees
9.4/10 Exceptional! (1,571 reviews)
Room was lean and well maintained

Reviewed on 16 Dec, 2025

The Hotel at Arundel Preserve
Days Inn by Wyndham Lanham Washington DC

Days Inn by Wyndham Lanham Washington DC

3 out of 5
9023 Annapolis Road/I-495 Lanham MD
Fully refundableReserve now, pay when you stay
The price is S$117 per night from 18 Jan to 19 Jan
S$117
18 Jan - 19 Jan, 2026
includes taxes & fees
8.2/10 Very Good! (1,012 reviews)
Good

Reviewed on 21 Dec, 2025

Days Inn by Wyndham Lanham Washington DC
See all 1,303 properties in Hillsmere
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 holiday package cost?
Live it up in Hillsmere from as little as . We offer a great selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few tours or experiences to your package.
How do I get a cheap travel package to Hillsmere?
Our Hillsmere holiday packages offer plenty of savings for the savvy traveller. For the best deals, simply bundle your hotel, flights and extras (including tours) into a handy package. But cheap prices are only the start of your next memorable adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels across the globe to choose from. Whatever your style or budget, there's a package here just for you.
Where should I stay in Hillsmere?
Most visitors who travel to Hillsmere include both U.S. Naval Academy and Maryland State House on their sightseeing itineraries. Why not go for a hotel near these popular attractions?
How far in advance should I book my Hillsmere holiday?
Browse Expedia to compare international flights as soon as you've got your travel dates. You can usually purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you have to book last minute, don't despair. Low prices to Hillsmere sometimes emerge a few weeks before departure.
What does an Expedia Hillsmere travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to create your perfect Hillsmere package. Once you've made your booking, you can add on the fun things like activities and tours. Don't forget, the more you bundle, the greater the savings!
What should I know before booking a Hillsmere travel package?
An Expedia travel package can be tailored to your budget and is a simple way to stretch your hard-earned dollars. How little or much you include is completely up to you. Hotels, rental cars and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a Hillsmere Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 airline partners worldwide, so you have options galore when putting together your Hillsmere trip.
If I'm not able to travel, can I cancel my Hillsmere holiday package?
It is possible to cancel your Hillsmere booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Things to do

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Ashes and Apparitions of Annapolis Ghost Tour

S$37
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Food Tour Plate

Historic Annapolis Food Tour

S$103
per adult
Historic Annapolis Food Tour
Ghosts of Annapolis: Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

S$47
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
See all activities in Annapolis

* 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.