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22 properties
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Search results showing properties in Highland Beach, Maryland, United States of America
Google map showing 22 properties
Photo gallery for Annapolis waterfront "tiny house" in garden setting
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Cottage · Epping Forest, 6.66 mi from Highland Beach
Annapolis waterfront "tiny house" in garden setting
Sleeps 4 · 1 bedroom · 1 bathroom
10/10
Exceptional
(208 reviews)
10 out of 10 Exceptional (208 reviews)
Unavailable
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Photo gallery for Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021
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Premier Host
Cottage · West Annapolis, 4.77 mi from Highland Beach
Amazing views, short walks to great dining!
Sleeps 4 · 1 bathroom
Private host
10/10
Exceptional
(65 reviews)
10 out of 10 Exceptional (65 reviews)
Unavailable
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Photo gallery for Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior
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Cottage · 7.68 mi from Highland Beach
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Sleeps 3 · 1 bedroom · 1 bathroom
Private host
9.8/10
Exceptional
(22 reviews)
9.8 out of 10 Exceptional (22 reviews)
Unavailable
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Cottage · Cape Saint Claire, 7.99 mi from Highland Beach
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Sleeps 5 · 1 bedroom · 1 bathroom
Private host
10/10
Exceptional
(60 reviews)
10 out of 10 Exceptional (60 reviews)
Unavailable
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Cottage · Hillsmere, 2.68 mi from Highland Beach
The Yellow Cottage on Harness Creek
Sleeps 6 · 2 bedrooms · 1 bathroom
Private host
10/10
Exceptional
(137 reviews)
10 out of 10 Exceptional (137 reviews)
Unavailable
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Cottage · 3.05 mi from Highland Beach
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Sleeps 11 · 3 bedrooms · 2 bathrooms
Private host
10/10
Exceptional
(186 reviews)
10 out of 10 Exceptional (186 reviews)
Unavailable
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Cottage · 7.3 mi from Highland Beach
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Sleeps 6 · 2 bedrooms · 2 bathrooms
Private host
10/10
Exceptional
(17 reviews)
10 out of 10 Exceptional (17 reviews)
Unavailable
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Cottage · Selby-on-the-Bay, 3.82 mi from Highland Beach
Waterfront nature retreat, contemporary home w/ pier by Annapolis. Pet Friendly!
Sleeps 7 · 3 bedrooms · 3 bathrooms
Private host
Unavailable
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Cottage · Epping Forest, 6.56 mi from Highland Beach
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Sleeps 7 · 3 bedrooms · 1 bathroom
Private host
9.8/10
Exceptional
(17 reviews)
9.8 out of 10 Exceptional (17 reviews)
Unavailable
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Cottage · Annapolis, 2.47 mi from Highland Beach
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.8/10
Exceptional
(20 reviews)
9.8 out of 10 Exceptional (20 reviews)
Unavailable
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Cottage · West Annapolis, 4.78 mi from Highland Beach
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Sleeps 6 · 3 bedrooms · 1+ bathroom
Private host
10/10
Exceptional
(20 reviews)
10 out of 10 Exceptional (20 reviews)
Unavailable
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Cottage · 5.55 mi from Highland Beach
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Sleeps 8 · 2 bedrooms · 3 bathrooms
Private host
Unavailable
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House · Riva, 7.01 mi from Highland Beach
Cheerful 3 bedroom home with ample space and parking on premise
Sleeps 6 · 3 bedrooms · 1 bathroom
Private host
9.4/10
Exceptional
(14 reviews)
9.4 out of 10 Exceptional (14 reviews)
Unavailable
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Cottage · Arnold, 8.34 mi from Highland Beach
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Sleeps 6 · 4 bedrooms · 3 bathrooms
Private host
10/10
Exceptional
(48 reviews)
10 out of 10 Exceptional (48 reviews)
Unavailable
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Cottage · Epping Forest, 6.15 mi from Highland Beach
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Sleeps 5 · 2 bedrooms · 1 bathroom
Private host
Unavailable
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Cottage · 9.4 mi from Highland Beach
Cozy waterfront remodeled beach cottage, just steps away from the Chesapeake Bay
Sleeps 8 · 4 bedrooms · 2 bathrooms
Private host
10/10
Exceptional
(10 reviews)
10 out of 10 Exceptional (10 reviews)
Unavailable
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Cottage · Annapolis, 2.96 mi from Highland Beach
Eastport Cozy Charmer
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.4/10
Exceptional
(3 reviews)
9.4 out of 10 Exceptional (3 reviews)
Unavailable
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Cottage · Eastport, 2.82 mi from Highland Beach
Coastal Chesapeake cottage in Eastport
Sleeps 7 · 4 bedrooms · 2 bathrooms
Private host
10/10
Exceptional
(1 review)
10 out of 10 Exceptional (1 review)
Unavailable
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