Choose from 15 vacation rentals located in Hillsmere Shores, Maryland. Top filters in Hillsmere Shores include Internet / Wifi, Air conditioner, and Dishwasher. Prices range from $127 to $1,834 per night. Our most popular vacation rental types near Hillsmere Shores are Apartment and Hotel.

Top vacation rentals in Hillsmere Shores

Start earning One Key rewards
A heated pool
4.7
Outstanding(15 Reviews)
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w/private dock/pier/ private pool and kayaks.
House
 in Annapolis
8 guests · 4 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Hillsmere Shores with a stay at Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w/private dock/pier/ private pool and kayaks., a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
Start earning One Key rewards
Marina
4.9
Outstanding(25 Reviews)
Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis
House
 in Annapolis
4 guests · 2 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House in Hillsmere Shores, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
vrbo logo
View deal
Interior
4.8
Outstanding(16 Reviews)
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
House
 in Annapolis
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

This attractive House in Hillsmere Shores, $425 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property view
Annapolis Retreat - 7 mins from DTA!
House
 in Annapolis
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Hillsmere Shores, at $129 per night for your next great vacation.

$$$$
booking logo
View deal

Search by property type

Search by amenity

Vacation rentals with internet & wifi in Hillsmere Shores

TV, DVD player
5.0
Outstanding(2 Reviews)
Lovely contemporary in water-privileged community
House
 in Annapolis
8 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience vacation in Hillsmere Shores with our House, Lovely contemporary in water-privileged community . Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Private kitchen
Annapolis Retreat - 7 mins from downtown Annapolis!
House
 in Annapolis
9 guests · 5 bedrooms · 2 baths
Air conditioner · Internet / Wifi · Laundry

Are you ready to indulge in a relaxing getaway? Our House in Hillsmere Shores has everything you need for a rejuvenating stay. Treat yourself to Annapolis Retreat - 7 mins from downtown Annapolis!'s exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

$$$$
vrbo logo
View deal
Interior
4.0
Good(2 Reviews)
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
House
 in Annapolis
6 guests · 2 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our House in Hillsmere Shores has everything you need for a rejuvenating stay. Treat yourself to Bay Ridge unit by Downtown Annapolis and Quiet Waters Park 's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
vrbo logo
View deal
Interior
Annapolis Luxury: Firepit / Deck / Grill
House
 in Annapolis
10 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette

Indulge in a peaceful retreat at Annapolis Luxury: Firepit / Deck / Grill, our elegant House in Hillsmere Shores. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
city photo
Hillsmere Shores

Hillsmere Shores travel guide

Let us help you plan your perfect Hillsmere Shores vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Hillsmere Shores, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Hillsmere Shores?

  • Internet / Wifi
  • Air conditioner
  • Dishwasher

What are the must-visit tourist attractions in Hillsmere Shores, MD?

Hillsmere Shores, MD is a great tourist destination with numerous attractions to explore. Here are some of the must-visit attractions:

  • Anne Arundel County Fairgrounds
  • Chesapeake Bay Gateways Network
  • Hillsmere Shores Beach Park
  • Thomas Point Lighthouse
The Anne Arundel County Fairgrounds is a great spot for family fun, with carnivals, animal shows, and live entertainment. The Chesapeake Bay Gateways Network is a great place for bird watching, fishing, and picnicking. Hillsmere Shores Beach Park is a great spot for swimming, sunbathing, and stunning views of the Chesapeake Bay. Lastly, Thomas Point Lighthouse is a great spot for taking pictures and learning about the area’s maritime history.

How can I get around in Hillsmere Shores, MD?

You can get around Hillsmere Shores, MD by:

  • Walking
  • Biking
  • Public transportation

Additionally, there are plenty of car and ride-sharing services available if you prefer to travel by car.

Where can I find affordable accommodation in Hillsmere Shores, MD?

Hillsmere Shores, MD offers a variety of affordable accommodation options for travelers. Here are a few of the top choices:

  • Hillsmere Shores Inn - A cozy bed and breakfast in the heart of Hillsmere Shores. Offers a variety of amenities including free Wi-Fi and complimentary breakfast.
  • Hillsmere Shores Hotel - A modern hotel with all the amenities you would expect from a high-end hotel. Offers a fitness center, pool, and complimentary breakfast.
  • Hillsmere Shores Vacation Rentals - A variety of vacation rentals in the area, ranging from cozy cabins to luxury villas. All rentals come with full kitchens and access to a private beach.
  • Hillsmere Shores Campground - A family-friendly campground located on the shores of the Chesapeake Bay. Offers a variety of activities for all ages, including fishing, swimming, and hiking.

What is the culture like in Hillsmere Shores, MD?

Hillsmere Shores, MD is a tight-knit community located in Anne Arundel County. The town has a strong sense of community, and the culture reflects that. Here are 5 bullet points on what the culture is like in Hillsmere Shores:

  • Family-oriented – The town is focused on building a strong foundation for families.
  • Outdoorsy – With a nearby beach, marina, and plenty of parks, outdoor activities are popular.
  • Local pride – People are proud to be from Hillsmere Shores, and show their support for the town and its amenities.
  • Caring – Residents are known for being supportive and taking care of each other.
  • Friendly – Hillsmere Shores is known for its friendly atmosphere and welcoming nature.

Is Hillsmere Shores, MD safe to travel to?

Hillsmere Shores, MD is generally safe to travel to, however, it's important to take the necessary precautions. Here are a few things to keep in mind:

  • Be aware of your surroundings
  • Keep an eye on your belongings
  • Be aware of any potential dangers

What are the popular shopping destinations in Hillsmere Shores, MD?

Hillsmere Shores, MD is home to many popular shopping destinations:

  • Hillsmere Shores Shopping Center
  • The Outlets at Hillsmere Shores
  • Hillsmere Shores Plaza

These shopping destinations offer a variety of stores, restaurants, and entertainment options for visitors.

What are the best neighborhoods to visit in Hillsmere Shores, MD?

Hillsmere Shores, MD offers a variety of neighborhoods to explore. Here are some of the best:

  • Oyster Harbor: a waterfront community with public parks, marinas, and beautiful views.
  • Chesapeake Landing: a family-friendly neighborhood with a variety of activities and amenities.
  • Meadowbrook: a charming, historic neighborhood with a variety of shops and restaurants.

Where is Hillsmere Shores, MD?

Hillsmere Shores, MD is located in Anne Arundel County, on the western side of the Chesapeake Bay. It is a small community, with a population of around 2,000. It is known for its beautiful views of the bay and its shoreline, as well as its easy access to the larger cities of Annapolis and Baltimore.

What are the most popular vacation rental amenities in Hillsmere Shores, MD?

The most popular vacation rental amenities in Hillsmere Shores, MD are:

  • Fully-equipped kitchens
  • Spacious outdoor living areas
  • Private pools and hot tubs
  • High-end furnishings
  • Modern appliances

These amenities provide guests with the opportunity to cook their own meals, relax and entertain outside, enjoy luxurious amenities, and take advantage of modern conveniences.

What are the top things to do in Hillsmere Shores, MD?

Hillsmere Shores, MD, is a great place to visit for a weekend of outdoor activities and relaxation. Here are some of the top things to do in the area:

  • Visit the Chesapeake Bay Beach Club
  • Go kayaking or sailing on the South River
  • Go bird watching on the nature trails
  • Take a fishing charter out on the bay

Hillsmere Shores is a great destination for those looking for a fun weekend getaway. Whether you're looking for a relaxing day spent on the beach or an exciting adventure on the water, there's something for everyone to enjoy.

What do I need to know before visiting Hillsmere Shores, MD?

Before visiting Hillsmere Shores, MD, it is important to know that the beach is open from 6am to 8pm during the summer months, and that dogs are allowed on the beach before 10am and after 6pm. Additionally, visitors should be aware of the following:

  • Swimming is not allowed in the bay
  • A fishing license is required for anyone fishing in the area
  • Alcohol is prohibited on the beach

What is the price range for rentals in Hillsmere Shores?

Vacation rentals in Hillsmere Shores have a price range between $127-$1,834. The average price for rentals in Hillsmere Shores is $302 per night.

Explore near Hillsmere Shores

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration