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Hillsmere Shores Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Hillsmere Shores vacation rentals

Interior

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 SAR 939
SAR 2,367 total
includes taxes & fees
20 Jul - 21 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!
Exterior

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 SAR 287
SAR 967 total
includes taxes & fees
29 Jun - 30 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

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, (46 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 SAR 594
SAR 1,379 total
includes taxes & fees
12 Jul - 13 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV, stereo

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (17 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is SAR 233
SAR 402 total
includes taxes & fees
21 Jul - 22 Jul
Lower Level Loft - Adorable Studio Apt. Near BWI
Terrace/patio

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
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
The price is SAR 517
SAR 1,347 total
includes taxes & fees
30 Jun - 1 Jul
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
TV

Farmhouse 1BD 1BA, Central Loc!

Farmhouse 1BD 1BA, Central Loc!
Hanover
9.0 out of 10, Wonderful, (2 reviews)
"Friendly host and within driving distance to Annapolis! "
United States
Meghan
The price is SAR 364
SAR 847 total
includes taxes & fees
29 Jun - 30 Jun
Farmhouse 1BD 1BA, Central Loc!
Fridge, microwave, oven, stovetop

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (11 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is SAR 321
SAR 876 total
includes taxes & fees
29 Jun - 30 Jun
Cute, Cozy 2-bedroom house near Annapolis with water access
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is SAR 619
SAR 1,630 total
includes taxes & fees
30 Jun - 1 Jul
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Exterior

Cozy Retreat Near Fort Meade | Fire Pit

Cozy Retreat Near Fort Meade | Fire Pit
Severn
10.0 out of 10, Exceptional, (2 reviews)
"Arundel Mills was less than 5 minutes away. So many restaurants, retail and grocery stores. Loved sitting out back listening to the birds. My daughter even saw a ground hig and cut up apples fornhim. Comfy bed and cozy kitchen with everything we needed. Victor was very responsive to any issue I had. "
United States
Kristine D.
The price is SAR 402
SAR 1,623 total
includes taxes & fees
29 Jul - 30 Jul
Cozy Retreat Near Fort Meade | Fire Pit
Interior

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, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is SAR 642
SAR 1,426 total
includes taxes & fees
1 Jul - 2 Jul
Large 2 bedroom house with private parking in a nice neighborhood
Exterior detail

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 SAR 422
SAR 1,149 total
includes taxes & fees
30 Jun - 1 Jul
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is SAR 751
SAR 1,123 total
includes taxes & fees
29 Jun - 30 Jun
BAYSIDE BUNGALOW
Smart TV

Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC
Crofton
10.0 out of 10, Exceptional, (1 review)
"Host was very friendly and accommodating. The location is wonderful. Lots of shops and festivities nearby could not have asked for better. Her cat was also very friendly "
United States
Michaela C.
The price is SAR 433
SAR 579 total
includes taxes & fees
12 Jul - 13 Jul
Cozy 1-bedroom studio in pleasant Crofton with AC
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is SAR 725
SAR 2,102 total
includes taxes & fees
29 Jun - 30 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
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 SAR 589
SAR 1,567 total
includes taxes & fees
15 Jul - 16 Jul
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is SAR 943
SAR 1,794 total
includes taxes & fees
7 Jul - 8 Jul
Annapolis Garden Suite
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is SAR 808
SAR 1,029 total
includes taxes & fees
29 Jun - 30 Jun
Sailboat Experience in Annapolis
Smart TV

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 SAR 770
SAR 1,501 total
includes taxes & fees
27 Jul - 28 Jul
Bayside Cottage steps from Rock Hall Harbor
TV

Charming 1BD 1BA, Central Loc!

Charming 1BD 1BA, Central Loc!
Harmans Woods
2.0 out of 10, (1 review)
The price is SAR 439
SAR 935 total
includes taxes & fees
15 Jul - 16 Jul
Charming 1BD 1BA, Central Loc!
Outdoor pool

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.4 out of 10, Very Good, (12 reviews)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
United States
Stephen R A.
The price is SAR 792
SAR 1,027 total
includes taxes & fees
1 Jul - 2 Jul
Secluded Tiny Pool House -Private Pool -Self Check in
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Loved me room. Very nice hotel. I will stay there again when in the area!"
Randolph 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis

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?

Charming Annapolis WaterVIEW Home: Visitors like this Hillsmere Shores vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Hillsmere Shores?

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

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.