Title: Highland Beach Vacation Rentals from $232: Search Short-Term Rentals | Expedia.com

[Hotels in Highland Beach](https://expedia.com/Highland-Beach-Hotels.d553248634998823058.Travel-Guide-Hotels)[Car Rentals in Highland Beach](https://expedia.com/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide)[Highland Beach Vacation Packages](https://expedia.com/Highland-Beach.d553248634998823058.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg)  
###  
Bundle & Save  
Get more, spend less whenever you see Bundle & Save deals
- ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg)  
###  
OneKeyCash  
Earn OneKeyCash on all your eligible bookings
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg)  
###  
Upfront pricing  
We are not like the others - we include taxes and fees

## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=553248634998823058&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=553248634998823058&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=553248634998823058&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=553248634998823058&startDate=2026-06-26&endDate=2026-06-28&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)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.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)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

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

9.6/10

Exceptional

(34 reviews)

"Great stay, would do it again."

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

Brandon D.

$219 nightly

$232 total

Mar 8 - Mar 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)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.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)

### Vacation Home in Stevensville

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

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.

$261 nightly

$276 total

Mar 10 - Mar 11

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)

![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)

![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)

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

### Vacation Home in Grasonville

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

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.

$397 nightly

$421 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/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/70000000/69550000/69541400/69541327/28005d62.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)

### Vacation Home in North Beach

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

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.

$293 nightly

$323 total

Mar 9 - Mar 10

Total with taxes and fees

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

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

### Vacation Home in Arnold

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

9.4/10

Exceptional

(36 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.

$278 nightly

$317 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.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)

### Vacation Home in Annapolis

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

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

Mar 8 - Mar 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)

![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)

![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)

![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)

### Apartment in Annapolis

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

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

$363 nightly

$414 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/491acaae.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)

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

### Apartment in Cape Saint Claire

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

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.

$343 nightly

$391 total

Mar 8 - Mar 9

Total with taxes and fees

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

![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)

### Vacation Home in South Gate

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

9.4/10

Exceptional

(14 reviews)

"No complaints"

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

Shelby B.

$99 nightly

$113 total

Mar 8 - Mar 9

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/101000000/100210000/100202700/100202663/f3add354.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)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/98bec3d6.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)

### Vacation Home in Admiral Heights

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

9.8/10

Exceptional

(8 reviews)

"Great property. Third time staying at property while visiting Annapolis. "

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

Holly W.

$457 nightly

$517 total

Mar 8 - Mar 9

Total with taxes and fees

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

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

### Houseboat in Pasadena

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

$383 nightly

$436 total

Mar 8 - Mar 9

Total with taxes and fees

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

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f0fc07ee.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)

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

### Vacation Home in Annapolis

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

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.

$321 nightly

$367 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.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/84000000/83930000/83922000/83921931/21befbf7.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)

### Vacation Home in Rock Hall

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

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.

$353 nightly

$374 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/b40492dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/e5b3706d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Beach

[](https://www.expedia.com/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information)

10/10

Exceptional

(32 reviews)

"Perfect place to spend quality time with our three adult children and their significant others. "

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

Malarkey F.

$388 nightly

$428 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.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)

![Marina](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/14020520.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)

### Houseboat in Arnold

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

9.8/10

Exceptional

(7 reviews)

"Great place!"

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

Chris A.

$329 nightly

$375 total

Mar 8 - Mar 9

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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/5d7daf3b.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)

### Vacation Home in Herald Harbor

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

10/10

Exceptional

(1 review)

"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."

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

Katherine P.

$191 nightly

$218 total

Mar 16 - Mar 17

Total with taxes and fees

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

![Marina](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/9b7348ba.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)

### Mobile Home in Edgewater

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

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

Mar 15 - Mar 16

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/681a375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/8aaef683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Shady Side

[](https://www.expedia.com/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Would stay here again "

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

Thomas D.

$390 nightly

$444 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.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/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Historic District

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

10/10

Exceptional

(75 reviews)

"Welcoming host, great location and easy parking "

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

Chris B.

$290 nightly

$331 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-5f725067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-97b0328a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h508x0y136-4ba3382c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w642h780x229y0-93850baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Burnie

[](https://www.expedia.com/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

8.8/10

Excellent

(9 reviews)

"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."

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

Jeffrey S.

$327 nightly

$373 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.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=2026-03-21&endDate=2026-03-22&regionId=553248634998823058&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_553248634998823058)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=HOUSE_BOAT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Highland+Beach%2C+Maryland%2C+United+States+of+America&regionId=553248634998823058&latLong=38.930389%2C-76.46579&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VILLA)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Beach-Vacation-Rentals.d553248634998823058.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Beach-Vacation-Rentals.d553248634998823058.Travel-Guide-VacationRentals)

## Top Highland Beach Hotel Reviews

![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e_y.jpg)

### Hampton Inn & Suites Annapolis

8/10 Good

"The hotel was good and clean the only thing I had a problem with is that I had to pay $10 a day for parking. How did they know I had a car. They never asked just assumed "

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

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg)

### Hilton Garden Inn Annapolis Downtown

8/10 Good

"The hotel was nice the room comfortable and spacious. The front desk staff was attentive and present. The location was in the center of town and close to everything. I hated the parking, the spaces were tight and somewhat limited but that is to be expected the hotel is in a very historic part of the city so the availability of a broad spacious parking lot was not expected. I am happy there was parking available and I did not need to move my car because of the great location. "

[](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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

10/10 Excellent

"So clean and smells so fresh! Great hot shower. Really clean and comfortable bed. Worth the money"

[](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

"Great rooms. "

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

8/10 Good

"Room very clean I don’t like that they didn’t have Disney jr just regular Disney so it wasn’t appropriate for my daughter to watch "

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

![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg)

### Rod 'N' Reel Resort

10/10 Excellent

"The entire building was clean, and comfortable. The room was decorated well and had a comfortable atmosphere. It’s just a little confusing when checking in, you have to go inside and then into another building. Maybe there could be a sign pointing to the entrance where you have to go to check in. "

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

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"I stayed here as I did a visit for my youngest son who is attending Bowie. While I stayed most of the time on campus, I found when I was at the hotel I found the staff and facility both inviting, warm and cordial. "

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

4/10 Poor

"Not welcoming "

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

10/10 Excellent

"Yes, the room was perfectly clean"

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

## Find out more about Highland Beach

**Everything you need to know about Highland Beach 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 Highland Beach 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 Highland Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Highland Beach vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Highland Beach. 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 Highland Beach 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 $232 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 Highland Beach rentals**

At Expedia, we put the best Highland Beach 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 Highland Beach 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 Highland Beach 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 Highland Beach. 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

- Trending destinations on Expedia.com
- All accommodation types in Highland Beach

### Trending destinations on Expedia.com

- [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals)
- [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals)
- [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals)
- [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals)
- [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals)
- [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals)
- [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals)
- [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals)
- [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals)
- [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)
- [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals)
- [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals)
- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [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 Highland Beach ](https://expedia.com/Highland-Beach-Private-Vacation-Homes.d553248634998823058-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Highland Beach ](https://expedia.com/Highland-Beach-Cottages.d553248634998823058-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Highland Beach ](https://expedia.com/Highland-Beach-Apartments.d553248634998823058-aaApartments.Travel-Guide-Accommodation)
- [B&B in Highland Beach ](https://expedia.com/Highland-Beach-Bed-And-Breakfast.d553248634998823058-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Highland Beach ](https://expedia.com/Highland-Beach-Houseboats.d553248634998823058-aaHouseboats.Travel-Guide-Accommodation)
- [Condo Rentals in Highland Beach ](https://expedia.com/Highland-Beach-Condos.d553248634998823058-aaCondos.Travel-Guide-Accommodation)
- [Motels in Highland Beach ](https://expedia.com/Highland-Beach-Motels.d553248634998823058-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Highland Beach ](https://expedia.com/Highland-Beach-Guest-Houses.d553248634998823058-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Highland Beach ](https://expedia.com/Highland-Beach-Agritourism.d553248634998823058-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Highland Beach ](https://expedia.com/Highland-Beach-Villas.d553248634998823058-aaVillas.Travel-Guide-Accommodation)
- [Inns in Highland Beach ](https://expedia.com/Highland-Beach-Inns.d553248634998823058-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland Beach ](https://expedia.com/Highland-Beach-Cabins.d553248634998823058-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Highland Beach?

### What are some of the best vacation home rentals that Highland Beach has to offer?

### What’s there to see and do in Highland Beach?

### What’s a vacation rental in Highland Beach like?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app