Airbnb, Vacation Rentals in Highland Beach, MD

Compare 1,626 available, short term beachfront holiday vacation home properties, starts from $14

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Airbnb, Vacation rentals and hotel deals in Highland Beach, MD

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
10 (73 reviews)
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Apartment · 2 Guests · 1 Bedroom
$163 /night*
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Village Inn
Village Inn
Village Inn
Village Inn
6.1 (150 reviews)
Village Inn
Motel · 2 Guests · 1 Bedroom
$125 /night
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
9.8 (41 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Holiday home · 2 Guests · 1 Bedroom
$233 /night*
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Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
7.8 (276 reviews)
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$102 /night
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Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
8.8 (589 reviews)
Country Inn & Suites by Radisson, Annapolis, MD
Hotel · 2 Guests · 1 Bedroom
$110 /night
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Modern Coastal Retreat
Modern Coastal Retreat
Modern Coastal Retreat
Modern Coastal Retreat
9.8 (7 reviews)
Modern Coastal Retreat
Holiday home · 2 Guests · 1 Bedroom
$100 /night*
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Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
10 (1 review)
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Accommodation · 2 Guests · 1 Bedroom
$200 /night*
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The Westin Annapolis
The Westin Annapolis
The Westin Annapolis
The Westin Annapolis
8.4 (330 reviews)
The Westin Annapolis
Hotel · 2 Guests · 1 Bedroom
$207 /night
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Hilton Garden Inn Kent Island
Hilton Garden Inn Kent Island
Hilton Garden Inn Kent Island
Hilton Garden Inn Kent Island
9.0 (248 reviews)
Hilton Garden Inn Kent Island
Hotel · 2 Guests · 1 Bedroom
$150 /night
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Best Western Annapolis
Best Western Annapolis
Best Western Annapolis
Best Western Annapolis
7.7 (396 reviews)
Best Western Annapolis
Hotel · 2 Guests · 1 Bedroom
$146 /night
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Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
8.3 (183 reviews)
Sonesta ES Suites Annapolis
Hotel · 2 Guests · 1 Bedroom
$152 /night
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Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
9.2 (25 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Apartment · 2 Guests · 1 Bedroom
$185 /night*
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Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
9.2 (5 reviews)
Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
Guest house · 2 Guests · 1 Bedroom
$215 /night*
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Hyatt Place Kent Narrows And Marina
Hyatt Place Kent Narrows And Marina
Hyatt Place Kent Narrows And Marina
Hyatt Place Kent Narrows And Marina
9.2 (189 reviews)
Hyatt Place Kent Narrows And Marina
Hotel · 2 Guests · 1 Bedroom
$139 /night
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Private Cottage on gated estate
Private Cottage on gated estate
Private Cottage on gated estate
Private Cottage on gated estate
10 (15 reviews)
Private Cottage on gated estate
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
7.9 (447 reviews)
Best Western Kent Narrows Inn
Hotel · 2 Guests · 1 Bedroom
$85 /night
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TownePlace Suites Bowie Town Center
TownePlace Suites Bowie Town Center
TownePlace Suites Bowie Town Center
TownePlace Suites Bowie Town Center
9.2 (188 reviews)
TownePlace Suites Bowie Town Center
Hotel · 2 Guests · 1 Bedroom
$154 /night
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Red Roof Inn Annapolis
Red Roof Inn Annapolis
Red Roof Inn Annapolis
Red Roof Inn Annapolis
7.2 (87 reviews)
Red Roof Inn Annapolis
Motel · 2 Guests · 1 Bedroom
$83 /night
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Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
10 (10 reviews)
Charming Downtown 3rd Floor 1 Bedroom Apt
Apartment · 2 Guests · 1 Bedroom
$192 /night*
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Historic Inns of Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
8.9 (1085 reviews)
Historic Inns of Annapolis
Hotel · 2 Guests · 1 Bedroom
$184 /night
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Vacation Destinations Near Highland Beach, MD

Airbnb, Holiday Beachfront House with Air Conditioning in Highland Beach, MD

Moore space
Moore space
Moore space
Moore space
Air Conditioning
Moore space
Holiday home · 2 Guests · 1 Bedroom
$210 /night
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Mini Suite
Mini Suite
Mini Suite
Mini Suite
Air Conditioning
Mini Suite
B & B · 2 Guests · 1 Bedroom
$421 /night
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How Does The Amenity Info Looks Like at Highland Beach, MD?
Best Amenities in Highland Beach, MD
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Check above for the most common and the least popular rental amenities in Highland Beach, and pick the one that fits your preference easily. In Highland Beach, 784 rentals offer Internet or Wifi, 733 rentals offer Air Conditioning, 697 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Most Typical in Highland Beach, MD Area?
Vacation House & Apartment Rental Price Information in Highland Beach, MD
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The graph shows the percentages of vacation homes in each price bucket. Highland Beach has the largest percentage (19.76%) of homes in $500+ price range.
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$500 +
$500 +
Which Accommodations Should I Pick in Highland Beach, MD?
Rental Property Types in Highland Beach, MD
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Before visiting Highland Beach, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Apartment, Studio, Cottage, Townhome, Condo, Estate, Guest House, Hotel, Bed And Breakfast, Boat, Bungalow, Hotel Suites, Lodge, Farmhouse, Villa, Yacht, Cabin, Resort, Chalet. House is the most-liked rental type, with the largest percentage of 57.69%. The biggest home in this area available for rent is around 48438 square feet.The least popular accommodation in Highland Beach is Chalet rentals
How Many Rental Accommodations Are Pets Friendly in Highland Beach, MD?
Pets Allowed vs Not Allowed in Highland Beach, MD
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21.53% of vacation homes in Highland Beach are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Where Should We Visit in Highland Beach, MD Area?
Must Visit Places In Highland Beach, MD
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The most common & popular places (a.k.a points of interests) here in Highland Beach are:

Which Airports Should I Choose To Get To Highland Beach, MD?
Suggested Airports in Highland Beach, MD
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Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Highland Beach, MD

Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Full Kitchen
9.8 (66 reviews)
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Holiday home · 2 Guests · 1 Bedroom
$649 /night*
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Full Kitchen
10 (7 reviews)
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Holiday home · 2 Guests · 1 Bedroom
$240 /night*
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Full Kitchen
9.8 (41 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Holiday home · 2 Guests · 1 Bedroom
$233 /night*
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Airbnb, Vacation Cottage with Fireplace in Highland Beach, MD

Grasonville Home w/ Private Pool on the Water
Grasonville Home w/ Private Pool on the Water
Grasonville Home w/ Private Pool on the Water
Grasonville Home w/ Private Pool on the Water
Fireplace
Grasonville Home w/ Private Pool on the Water
Cottage · 2 Guests · 1 Bedroom
$473 /night
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'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
Fireplace
9.4 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 2 Guests · 1 Bedroom
$255 /night*
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Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Fireplace
9.4 (112 reviews)
Eastern Shore Getaway Near St. Michaels
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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