Hillsmere Shores Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Hillsmere Shores vacation rentals

Marina

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 ￥27,468
￥77,282 total
includes taxes & fees
Apr 27 - Apr 28
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 ￥28,529
￥85,941 total
includes taxes & fees
Apr 27 - Apr 28
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (9 reviews)
"Great place!"
United States
Chris A.
The price is ￥22,759
￥57,015 total
includes taxes & fees
Apr 27 - Apr 28
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is ￥21,516
￥60,504 total
includes taxes & fees
Apr 27 - Apr 28
Waterfront Unit | Dock, Kayaks & SUPs Included
Terrace/patio

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ￥34,809
￥79,654 total
includes taxes & fees
May 4 - May 5
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is ￥12,352
￥40,969 total
includes taxes & fees
Apr 28 - Apr 29
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ￥30,402
￥61,792 total
includes taxes & fees
May 26 - May 27
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (20 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 ￥13,724
￥52,469 total
includes taxes & fees
Apr 27 - Apr 28
Walk to Beach! King Bed & Free Beach Passes
Dining

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)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is ￥39,845
￥66,732 total
includes taxes & fees
Apr 27 - Apr 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is ￥21,516
￥52,327 total
includes taxes & fees
Apr 29 - Apr 30
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is ￥27,892
￥57,948 total
includes taxes & fees
May 11 - May 12
Bayside Cottage steps from Rock Hall Harbor
1 bedroom, desk, free WiFi, bed sheets

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (15 reviews)
"I’m late on this review but I still remember my stay a few weeks ago. The place was great and extremely welcoming. We had a wonderful time staying here!"
United States
MAD J.
The price is ￥9,882
￥16,716 total
includes taxes & fees
Apr 27 - Apr 28
Lower Level Loft - Adorable Studio Apt. Near BWI
Outdoor dining

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, (33 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥15,809
￥64,979 total
includes taxes & fees
Apr 27 - Apr 28
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥28,688
￥43,925 total
includes taxes & fees
May 5 - May 6
BAYSIDE BUNGALOW
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (2 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ￥36,817
￥76,911 total
includes taxes & fees
Apr 29 - Apr 30
Sunset Cottage - West River Access and Views!
Outdoor pool

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (11 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is ￥17,532
￥23,620 total
includes taxes & fees
Apr 29 - Apr 30
Secluded Tiny Pool House -Private Pool -Self Check in
Dining

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ￥33,608
￥84,281 total
includes taxes & fees
May 3 - May 4
Charming Pet-Friendly Stay - Near Bay & Beaches.
Outdoor pool, a heated pool

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
The price is ￥39,447
￥74,222 total
includes taxes & fees
Apr 27 - Apr 28
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is ￥28,688
￥96,297 total
includes taxes & fees
Apr 27 - Apr 28
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Microwave, oven, stovetop, dishwasher

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (5 reviews)
The price is ￥13,627
￥36,429 total
includes taxes & fees
Apr 30 - May 1
Cute, Cozy 2-bedroom house in near Annapolis with water access
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Our door keypad didn’t work. It would light up green but not unlock."
Emily 1-night trip
Posted 12 hours ago
Rod 'N' Reel Resort

Find out more about Hillsmere Shores

Search for holiday rentals in Hillsmere Shores on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsmere Shores using one of the methods below:

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Look no further and take a look at our great range of rental properties in Hillsmere Shores!

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 9 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 Bay Ridge Beach.

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.