Hillsmere Shores Holiday Rentals

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Our top choices for Hillsmere Shores holiday rentals

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
The price is AU$672
includes taxes & fees
16 Feb - 17 Feb
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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.
The price is AU$720
includes taxes & fees
16 Feb - 17 Feb
Annapolis Retreat - 7 mins from downtown Annapolis!

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

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Edgewater
The price is AU$4,342
includes taxes & fees
16 Feb - 17 Feb
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

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.
The price is AU$356
includes taxes & fees
17 Feb - 18 Feb
Charming Coastal/Country Home w/3 Acres & Sauna!

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.2 out of 10, Wonderful, (5 reviews)
The price is AU$789
includes taxes & fees
16 Feb - 17 Feb
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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.
The price is AU$592
includes taxes & fees
16 Feb - 17 Feb
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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.
The price is AU$508
includes taxes & fees
18 Feb - 19 Feb
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is AU$615
includes taxes & fees
16 Feb - 17 Feb
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.

Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.
Ferndale
10.0 out of 10, Exceptional, (2 reviews)
"Nice place. Donald was accommodating. Good location. "
United States
William D.
The price is AU$547
includes taxes & fees
16 Feb - 17 Feb
Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$997
includes taxes & fees
2 Mar - 3 Mar
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Deale
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful property! Water on two sides, lots of outdoor space , we had 11 people from 2-92 years staying for almost a week and had a great time. Wonderful sitting areas and screened porch. We crabbed, kayaked, had a campfire grilled. Relaxing getaway"
United States
Jody P.
The price is AU$1,043
includes taxes & fees
18 Feb - 19 Feb
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is AU$556
includes taxes & fees
16 Feb - 17 Feb
Sunset Cottage - West River Access and Views!

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.
The price is AU$346
includes taxes & fees
17 Feb - 18 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
The price is AU$314
includes taxes & fees
16 Mar - 17 Mar
Cute, Cozy 2-bedroom house in near Annapolis with water access

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.
The price is AU$466
includes taxes & fees
1 Mar - 2 Mar
Large 2 bedroom house with private parking in a nice neighborhood

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.
The price is AU$616
includes taxes & fees
22 Feb - 23 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!
Historic District
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AU$951
includes taxes & fees
17 Feb - 18 Feb
Fisher House: Steps From USNA + Covered Parking!

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.
The price is AU$769
includes taxes & fees
26 Feb - 27 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$721
includes taxes & fees
17 Feb - 18 Feb
Fabulous 5-bedroom house with AC in charming Annapolis

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is AU$599
includes taxes & fees
28 Feb - 1 Mar
40' Bristol sailboat with spectacular views
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsmere Shores holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hillsmere Shores holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsmere Shores holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsmere Shores holiday rentals we have selected for you start as low as AU$1,326 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillsmere Shores rentals

At Expedia, we put the best Hillsmere Shores holiday 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 holiday.

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 holiday rental in Hillsmere Shores?

Yes, there are holiday rentals close to the most popular sights in Hillsmere Shores, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Hillsmere Shores has to offer?

The Blue Crab Beach House - Free beach passes : This holiday home rental outside of Hillsmere Shores is located near the beach, and has a fireplace, a patio and a BBQ 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 garden and a selection of games.

How many holiday rentals are there in Hillsmere Shores?

Expedia has 10 holiday 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 wider area, you’ll find Kunta Kinte–Alex Haley Memorial and Bay Ridge Beach.

What’s a holiday rental in Hillsmere Shores like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillsmere Shores. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.