Default HTG hotel image

Hillsmere Shores Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Hillsmere Shores holiday rentals

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$1,026
includes taxes & fees
4 Aug - 5 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is NZ$739
includes taxes & fees
29 July - 30 July
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$473
includes taxes & fees
28 July - 29 July
BAYSIDE BUNGALOW

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is NZ$611
includes taxes & fees
3 Aug - 4 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!

Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (1 review)
"Great spot! Amazing amount of room. Great communication in ease of check-in"
United States
Jeffrey T.
The price is NZ$2,013
includes taxes & fees
19 July - 20 July
Waterfront Escape with Pool Nature Lover Paradise

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, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is NZ$450
includes taxes & fees
15 July - 16 July
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is NZ$1,484
includes taxes & fees
20 July - 21 July
Charming Annapolis WaterVIEW Home

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
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is NZ$1,239
includes taxes & fees
22 July - 23 July
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$1,202
includes taxes & fees
22 July - 23 July
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (14 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is NZ$1,192
includes taxes & fees
15 July - 16 July
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is NZ$870
includes taxes & fees
1 Aug - 2 Aug
Pool Loft Suite | Bay Access & Beach Passes

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$884
includes taxes & fees
15 July - 16 July
Waterfront Oasis of Annapolis Star

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is NZ$527
includes taxes & fees
15 July - 16 July
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
Chic retreat steps to Water, Piers & Waterfront Park

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, (37 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is NZ$1,949
includes taxes & fees
31 July - 1 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is NZ$1,084
includes taxes & fees
11 Aug - 12 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is NZ$709
includes taxes & fees
22 July - 23 July
Beachside Oasis with Beach Passes & King Suite by A Haven Away

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
The price is NZ$1,188
includes taxes & fees
15 July - 16 July
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
8.8 out of 10, Excellent, (8 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is NZ$1,177
includes taxes & fees
28 July - 29 July
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic District
10.0 out of 10, Exceptional, (1 review)
Historic Downtown Luxury • USNA • Waterfront
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$273 per night. Entering your travel dates in the search wizard you might find 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?

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Hillsmere Shores is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Hillsmere Shores?

Expedia has 8 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 Annapolis Landing Marina and Maryland Hall for Creative Arts.

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.