Title: Hillsmere Shores Vacation Rentals from $233: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=553248634998892012&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248634998892012&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=553248634998892012&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=553248634998892012&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Hillsmere Shores vacation rentals

![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f2ba56b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f79dd58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bay Ridge unit by Downtown Annapolis and Quiet Waters Park 

[](https://www.expedia.com/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

Annapolis

8.8/10

Excellent

(3 reviews)

"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

$425 nightly

$485 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/d00ee2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/a72fcd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/48c7542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Retreat - 7 mins from downtown Annapolis!

[](https://www.expedia.com/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

Hillsmere

10/10

Exceptional

(6 reviews)

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul C.

$476 nightly

$543 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/4b955546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/9c7dbc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/10010e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/d131334a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

Arnold

9.8/10

Exceptional

(8 reviews)

"Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris A.

$334 nightly

$381 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/b1ed4047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/852031b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/cc9a4892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/139d479a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

[](https://www.expedia.com/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

Pasadena

$395 nightly

$450 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/54c5a0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/63fb220b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/9b7348ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Unit | Dock, Kayaks & SUPs Included

[](https://www.expedia.com/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information)

Edgewater

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel K.

$289 nightly

$329 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/55152f23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/3d3727e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/6a4e6884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/073cfcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

[](https://www.expedia.com/Annapolis-Hotels-Annapolis-Gem-Tranquil-4-BR-Murray-Hill-Victorian.h128417470.Hotel-Information)

Historic District

$448 nightly

$507 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Annapolis-Gem-Tranquil-4-BR-Murray-Hill-Victorian.h128417470.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(35 reviews)

"Great stay, would do it again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandon D.

$220 nightly

$233 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

Stevensville

9.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Supriya V.

$229 nightly

$242 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe C.

$395 nightly

$419 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a70d4b32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

[](https://www.expedia.com/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

Exceptional

(38 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Traci L.

$288 nightly

$328 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/ce9b7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/4cfce214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Cottage steps from Rock Hall Harbor

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

Rock Hall

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dorothy R.

$343 nightly

$364 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/457a4a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/42bbbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! King Bed & Free Beach Passes

[](https://www.expedia.com/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

North Beach

10/10

Exceptional

(19 reviews)

"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elaine D.

$312 nightly

$345 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/197cec39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/a815bd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/b3eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/61b9de4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Tiny Pool House -Private Pool -Self Check in

[](https://www.expedia.com/Glen-Burnie-Hotels-CLEAN.h109465066.Hotel-Information)

Glen Burnie

8.6/10

Excellent

(10 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellie F.

$125 nightly

$142 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Glen-Burnie-Hotels-CLEAN.h109465066.Hotel-Information)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88430000/88428300/88428230/cf93c0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88430000/88428300/88428230/53c8c9c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88430000/88428300/88428230/b5ec6469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88430000/88428300/88428230/cec3d3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lower Level Loft - Adorable Studio Apt. Near BWI

[](https://www.expedia.com/Millersville-Hotels-Adorable-Studio-Apt-Near-BWI.h88428230.Hotel-Information)

South Gate

9.4/10

Exceptional

(14 reviews)

"No complaints"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shelby B.

$94 nightly

$107 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Millersville-Hotels-Adorable-Studio-Apt-Near-BWI.h88428230.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/bb91d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/3f9288e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/ea596829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Home | Fenced Yard | Pool Table | 10 Guests

[](https://www.expedia.com/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

Cape Saint Claire

9.8/10

Exceptional

(11 reviews)

"Enjoyed our stay- thank you!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

KateriK

$500 nightly

$570 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1746x0y0-fc1adaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/2b0352ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/68ce83bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1729x0y0-ae4201db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BAYSIDE BUNGALOW

[](https://www.expedia.com/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

Rock Hall

10/10

Exceptional

(52 reviews)

"Very quaint and quiet place to stay. Very relaxing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roger

$278 nightly

$295 total

Apr 30 - May 1

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/35e98514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/c2958ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information)

Arundel on the Bay

9.6/10

Exceptional

(13 reviews)

"Great communication with the host, easy check in.. nice property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Henry P.

$512 nightly

$584 total

Apr 28 - Apr 29

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information)

![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/1e2f03eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f21ef3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f5323c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 40' Bristol sailboat with spectacular views

[](https://www.expedia.com/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

Stevensville

$409 nightly

$434 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.com/Annapolis-Hotels-Comfy-Oasis.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas

$409 nightly

$466 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Comfy-Oasis.h68986275.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/9d27d09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/c889c2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/8f010e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/dd15abfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

Herald Harbor

9.6/10

Exceptional

(4 reviews)

"Just as advertised no issues. Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dan O.

$206 nightly

$235 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&regionId=553248634998892012&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Hillsmere+Shores%2C+Maryland%2C+United+States+of+America&regionId=553248634998892012&latLong=38.940116%2C-76.494962&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=HOUSE_BOAT)

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## Top Hillsmere Shores Hotel Reviews

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/aecf0353_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

4/10 Poor

"The property had an issue with no cold water, and "

[](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information)

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg)

### Crowne Plaza Annapolis by IHG

6/10 Okay

"Would have been nice to know when booking (or in advance) that the jacuzzi was out of service. I was looking forward to that. For the name sake, there was nothing special about this hotel. Would have been nice to have an included breakfast for the price."

[](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Super spacious and clean. Would stay again"

[](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"I enjoyed my stay. The staff was friendly and the room was clean. The breakfast provided had a great variety. The only draw back was the pool hours. I didn’t get to enjoy it as the two days I was there it was closed one day and the other day I was out exploring the area and DC so by time I came back it was already closed. "

[](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![Microtel Inn & Suites by Wyndham Gambrills](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg)

### Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent

"Excellent staff at Hotel"

[](https://expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information)

![Holiday Inn Express I-95 Capitol Beltway-Largo by IHG](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/fb2063de_y.jpg)

### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

2/10 Terrible

"Extremely noisy!!!! Left the hotel that night"

[](https://expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Beautiful hotel. Great location. Friendly staff. "

[](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09_y.jpg)

### DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"I loved this property because it was in a secluded location and they allowed me to check in prior to three. the room was nice and the front desk staff were pleasant and offered me suggestions to visit the town."

[](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information)

![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg)

### SpringHill Suites by Marriott Annapolis

4/10 Poor

"The room did not have a fresh smell, toilet clogged. No new sheets or cleaned room 2 nd day"

[](https://expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information)

## 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 $233 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.

## Explore a world of travel with Expedia

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- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Private-Vacation-Homes.d553248634998892012-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Apartments.d553248634998892012-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Cottages.d553248634998892012-aaCottages.Travel-Guide-Accommodation)
- [B&B in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Bed-And-Breakfast.d553248634998892012-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Houseboats.d553248634998892012-aaHouseboats.Travel-Guide-Accommodation)
- [Condo Rentals in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Condos.d553248634998892012-aaCondos.Travel-Guide-Accommodation)
- [Motels in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Motels.d553248634998892012-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Guest-Houses.d553248634998892012-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Villas.d553248634998892012-aaVillas.Travel-Guide-Accommodation)
- [Inns in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Inns.d553248634998892012-aaInns.Travel-Guide-Accommodation)
- [Farmstay in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Agritourism.d553248634998892012-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Hillsmere Shores ](https://expedia.com/Hillsmere-Shores-Apart-Hotels.d553248634998892012-aaApartHotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Hillsmere Shores?

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