Title: Highland Beach Vacation Rentals from CA $1,243: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highland Beach vacation rentals

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.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)

![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)

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

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

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

Stevensville

9.6/10

Exceptional

(33 reviews)

"Great stay, would do it again."

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

Brandon D.

CA $87

CA $334 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/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)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.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)

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

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

Stevensville

9.8/10

Exceptional

(43 reviews)

"We had a great stay! The property has everything we needed and host was easy to communicate with "

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

Stephanie S.

CA $87

CA $334 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.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)

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

[](https://www.expedia.ca/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.

CA $340

CA $574 total

includes taxes & fees

Feb 23 - Feb 24

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

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.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)

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

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

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

North Beach

10/10

Exceptional

(19 reviews)

"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"

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

Jennifer B.

CA $111

CA $445 total

includes taxes & fees

Feb 22 - Feb 23

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

![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.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)

![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)

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

[](https://www.expedia.ca/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

CA $235

CA $657 total

includes taxes & fees

Feb 23 - Feb 24

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

![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.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.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.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

CA $282

CA $561 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.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/90000000/89060000/89057700/89057630/3a482076.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.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

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

Emily B.

CA $191

CA $459 total

includes taxes & fees

Mar 9 - Mar 10

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

![On the beach](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/66cb9c5e.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)

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

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

Pasadena

CA $215

CA $579 total

includes taxes & fees

Feb 18 - Feb 19

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/f3add354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/7efcfe99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/ab2cfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/465f6a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute bungalow blocks to Stadium

[](https://www.expedia.ca/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information)

Admiral Heights

9.8/10

Exceptional

(8 reviews)

"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"

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

Tammy L.

CA $222

CA $740 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/bc27c0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/91738a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f0fc07ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wright's Cottage- Pet's Welcome & EV Charging

[](https://www.expedia.ca/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information)

Annapolis

9.2/10

Wonderful

(16 reviews)

"Nice little spot, very quiet "

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

Susan S.

CA $225

CA $486 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.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)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/ea596829.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)

### Neptune by the Water - Pet Friendly Fenced Yard

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

Cape Saint Claire

9.8/10

Exceptional

(11 reviews)

"The house had everything we needed for a comfortable stay. We would definitely recommend this place."

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

Kelly D.

CA $218

CA $784 total

includes taxes & fees

Feb 23 - Feb 24

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

![TV](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/a2bc20d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/4624c991.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/af565df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/9d27d09a.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.ca/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

Herald Harbor

CA $104

CA $302 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Crownsville-Hotels-Cute.h124829757.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)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88430000/88428300/88428230/48399769.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)

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

[](https://www.expedia.ca/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.

CA $84

CA $154 total

includes taxes & fees

Mar 9 - Mar 10

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/8d73bbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/28c9186e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/a19fc40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Pool Loft sleeps 4

[](https://www.expedia.ca/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

Cape Saint Claire

10/10

Exceptional

(4 reviews)

"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."

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

Ana S.

CA $187

CA $552 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.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)

![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)

![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)

![Marina](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/14020520.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.ca/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

Arnold

9.8/10

Exceptional

(7 reviews)

"Enjoyed the stay"

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

Kedra B.

CA $179

CA $498 total

includes taxes & fees

Mar 2 - Mar 3

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

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/d339d550.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)

![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.ca/CLEAN.h109465066.Hotel-Information)

Glen Burnie

8.6/10

Excellent

(10 reviews)

"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"

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

Robert F.

CA $98

CA $143 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/CLEAN.h109465066.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2br home w/ parking in downtown Annapolis

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

Historic District

10/10

Exceptional

(74 reviews)

"Welcoming host, great location and easy parking "

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

Chris B.

CA $194

CA $464 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1514h908x8y2-08d635bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y2-e4e5546a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

Historic District

10/10

Exceptional

(5 reviews)

"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "

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

Tracie B.

CA $180

CA $961 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/708da323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/97debd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e33942cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e360a10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

[](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.Hotel-Information)

Glen Burnie

8.0/10

Very good

(2 reviews)

"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"

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

James D.

CA $123

CA $171 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.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)

![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)

![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)

![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)

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

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

Hillsmere

10/10

Exceptional

(5 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.

CA $217

CA $706 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.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.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&regionId=553248634998823058&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=HOUSE_BOAT)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VILLA)

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## Top Highland Beach Hotel Reviews

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg)

### Candlewood Suites Annapolis by IHG

10/10 Excellent

"The room was clean and comfortable. The stove was easy to use but there were 2 burners. Great room and stay "

[](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg)

### Hampton Inn & Suites Annapolis

10/10 Excellent

"Very nice place but why we have to pay for parking ,"

[](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information)

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg)

### Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Would stay here again"

[](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"We had a wonderful stay and really enjoyed it. The courtesy of the stuff was outstanding!"

[](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Great place. Perfect."

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

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "

[](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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

"Our room was clean and the staff was friendly. We plan to stay here again on future visits."

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

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Great stay. Room was great, staff were very friendly and helpful. "

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

![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg)

### Rod 'N' Reel Resort

10/10 Excellent

"Newly remodeled rooms. Very clean. Staff was so friendly and courteous! I love the fact there are two restaurants on site. "

[](https://expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information)

## Find out more about Highland Beach

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highland Beach. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Highland Beach ](https://expedia.ca/Highland-Beach-Private-Vacation-Homes.d553248634998823058-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Highland Beach ](https://expedia.ca/Highland-Beach-Cottages.d553248634998823058-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Highland Beach ](https://expedia.ca/Highland-Beach-Apartments.d553248634998823058-aaApartments.Travel-Guide-Accommodation)
- [B&B in Highland Beach ](https://expedia.ca/Highland-Beach-Bed-And-Breakfast.d553248634998823058-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Highland Beach ](https://expedia.ca/Highland-Beach-Houseboats.d553248634998823058-aaHouseboats.Travel-Guide-Accommodation)
- [Condo Rentals in Highland Beach ](https://expedia.ca/Highland-Beach-Condos.d553248634998823058-aaCondos.Travel-Guide-Accommodation)
- [Motels in Highland Beach ](https://expedia.ca/Highland-Beach-Motels.d553248634998823058-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Highland Beach ](https://expedia.ca/Highland-Beach-Guest-Houses.d553248634998823058-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Highland Beach ](https://expedia.ca/Highland-Beach-Agritourism.d553248634998823058-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Highland Beach ](https://expedia.ca/Highland-Beach-Villas.d553248634998823058-aaVillas.Travel-Guide-Accommodation)
- [Inns in Highland Beach ](https://expedia.ca/Highland-Beach-Inns.d553248634998823058-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland Beach ](https://expedia.ca/Highland-Beach-Cabins.d553248634998823058-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

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