Hillsmere Shores Vacation Rentals

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Our top choices for Hillsmere Shores vacation rentals

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$453 nightly
The price is $516
Feb 9 - Feb 10
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$425 nightly
The price is $485
Feb 8 - Feb 9
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
$321 nightly
The price is $366
Feb 9 - Feb 10
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Annapolis Boat Life - Overnight Stays

Annapolis Boat Life - Overnight Stays
ANNAPOLIS
10.0 out of 10, Exceptional, (1 review)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
$257 nightly
The price is $261
Mar 10 - Mar 11
Total with taxes and fees
Annapolis Boat Life - Overnight Stays

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$263 nightly
The price is $279
Feb 17 - Feb 18
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
$271 nightly
The price is $287
Feb 17 - Feb 18
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

Top Location | Free Breakfast + Fitness Center

Top Location | Free Breakfast + Fitness Center
Lanham
10.0 out of 10, Exceptional, (1 review)
"Very nice!"
United States
Kerry B.
$144 nightly
The price is $163
Feb 8 - Feb 9
Total with taxes and fees
Top Location | Free Breakfast + Fitness Center

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Feb 8 - Feb 9
Total with taxes and fees
Waterfront Oasis of Annapolis Star

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$342 nightly
The price is $390
Feb 8 - Feb 9
Total with taxes and fees
Luxury Pool Loft sleeps 4

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
$386 nightly
The price is $440
Feb 8 - Feb 9
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!"
United States
Emily B.
$280 nightly
The price is $319
Feb 11 - Feb 12
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
$416 nightly
The price is $474
Feb 9 - Feb 10
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
$416 nightly
The price is $474
Feb 8 - Feb 9
Total with taxes and fees
London Towne Bungalow w/Loft - Walk to the Beach!

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
$314 nightly
The price is $358
Feb 8 - Feb 9
Total with taxes and fees
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$369 nightly
The price is $408
Feb 11 - Feb 12
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
$209 nightly
The price is $212
Mar 2 - Mar 3
Total with taxes and fees
Sailboat Experience in Annapolis

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$453 nightly
The price is $516
Feb 9 - Feb 10
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Edgewater
$2,753 nightly
The price is $3,138
Feb 8 - Feb 9
Total with taxes and fees
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$396 nightly
The price is $420
Feb 9 - Feb 10
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.6 out of 10, Excellent, (8 reviews)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
$308 nightly
The price is $351
Feb 9 - Feb 10
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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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Top Hillsmere Shores Hotel Reviews

Find out more about Hillsmere Shores

Everything you need to know about Hillsmere Shores vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsmere Shores vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsmere Shores vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsmere Shores vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsmere Shores. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillsmere Shores in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $917 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillsmere Shores rentals

At Expedia, we put the best Hillsmere Shores vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillsmere Shores rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsmere Shores vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsmere Shores. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Hillsmere Shores?

Yes, there are vacation rentals near top attractions in Hillsmere Shores, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Hillsmere Shores?

The Blue Crab Beach House - Free beach passes : Visitors like this Hillsmere Shores vacation home rental. It is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

How many vacation rentals are there in Hillsmere Shores?

Expedia has 11 vacation rentals for your stay in Hillsmere Shores.

What’s there to see and do in Hillsmere Shores?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Maryland Quiet Waters Park. In the larger area, you’ll find Kunta Kinte–Alex Haley Memorial and Annapolis Landing Marina.

What’s a vacation rental in Hillsmere Shores like?

Vacation rentals are private accommodations you can book for a couple days or more in Hillsmere Shores. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.