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Here at VacationHomeRents, you can easily find and compare the best vacation apartments, cabins, house boats, beach houses, and RV deals. By a simple click, we help you search among millions of listings across the top sites like Airbnb, Vrbo, Booking.com and more.
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ACCOMMODATION TYPES

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

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
4.9 (61 reviews)
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Apartment · 2 Guests · 1 Bedroom
$170 /night*
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Hampton Inn & Suites Annapolis
4.1 (1300 reviews)
Hampton Inn & Suites Annapolis
Hotel · 1 Bedroom
$158 /night
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Private Apartment - Minutes to USNA
3.3 (6 reviews)
Private Apartment - Minutes to USNA
Holiday home · 4 Guests · 2 Bedrooms
$125 /night*
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Anchor's Away in the Heart of Eastport!
4.7 (23 reviews)
Anchor's Away in the Heart of Eastport!
Apartment · 2 Guests · 1 Bedroom
$169 /night*
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Hampton Inn & Suites Annapolis
4.0 (472 reviews)
Hampton Inn & Suites Annapolis
Hotel · 1 Bedroom
$158 /night
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Village Inn
3.0 (703 reviews)
Village Inn
Motel · 1 Bedroom
$96 /night
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Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
3.9 (1528 reviews)
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Hotel · 1 Bedroom
$127 /night
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Hilton Garden Inn Annapolis
4.1 (2194 reviews)
Hilton Garden Inn Annapolis
Hotel · 1 Bedroom
$159 /night
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Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Holiday home · 4 Guests · 2 Bedrooms
$150 /night*
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Airbnb, Holiday Beachfront House with Air Conditioning in Highland Beach, MD

Stay downtown with parking, backyard, and patio! 3 bd, 2.5 ba. Walk everywhere!
Air Conditioning
3.3 (18 reviews)
Stay downtown with parking, backyard, and patio! 3 bd, 2.5 ba. Walk everywhere!
Holiday home · 6 Guests · 3 Bedrooms
$633 /night*
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WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Air Conditioning
4.9 (34 reviews)
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage · 10 Guests · 5 Bedrooms
$608 /night*
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Flag House Inn
Air Conditioning
5.0 (60 reviews)
Flag House Inn
B & B · 1 Bedroom
$419 /night
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Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Highland Beach, MD

Charming Romantic, or Navy Professional Historic Retreat—Steps to City Dock!
Full Kitchen
Charming Romantic, or Navy Professional Historic Retreat—Steps to City Dock!
Holiday home · 8 Guests · 4 Bedrooms
$600 /night*
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Stay downtown with parking, backyard, and patio! 3 bd, 2.5 ba. Walk everywhere!
Full Kitchen
3.3 (18 reviews)
Stay downtown with parking, backyard, and patio! 3 bd, 2.5 ba. Walk everywhere!
Holiday home · 6 Guests · 3 Bedrooms
$633 /night*
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Private Cottage on gated estate
Full Kitchen
5.0 (3 reviews)
Private Cottage on gated estate
Holiday home · 6 Guests · 3 Bedrooms
$200 /night*
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Airbnb, Vacation Cottage with Fireplace in Highland Beach, MD

'Newer Cottage Incredibly and Comfortably Furnished.'
Fireplace
4.6 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 4 Guests · 2 Bedrooms
$255 /night*
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WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Fireplace
4.9 (34 reviews)
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage · 10 Guests · 5 Bedrooms
$608 /night*
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Airbnb, Pet Friendly Vacation Cottage in Highland Beach, MD

ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
Pets Welcome
4.9 (35 reviews)
ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
Cottage · 6 Guests · 3 Bedrooms
$550 /night*
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WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Pets Welcome
4.9 (34 reviews)
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage · 10 Guests · 5 Bedrooms
$608 /night*
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How Does The Amenity Info Looks Like at Highland Beach, MD?

Best Amenities in Highland Beach, MD

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

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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Which Accommodations Should I Pick in Highland Beach, MD?
Rental Property Types in Highland Beach, MD
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
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.
Which Airports Should I Choose To Get To Highland Beach, MD?
Suggested Airports in Highland Beach, MD
* 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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