Vacation rentals in Highland Beach
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Top-rated vacation rentals in Highland Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Edgewater
4.99 out of 5 average rating, 123 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.
Jan 21 – 28
Cottage in Annapolis
4.96 out of 5 average rating, 328 reviewsRelaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.
Mar 10 – 17
Cottage in Annapolis
4.94 out of 5 average rating, 308 reviewsWright’s Cottage, Pets Welcome!
We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!
Aug 20 – 27
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Highland Beach vacation rentals
Other great vacation rentals in Highland Beach
Loft in Annapolis
4.91 out of 5 average rating, 910 reviewsStep Out to Main Street From a Chic Loft
Jan 13 – 20
Guest suite in Arnold
4.94 out of 5 average rating, 110 reviewsCoastal Comfort Suite Near Annapolis, Hottub, EV
Jul 15 – 22
Guesthouse in Stevensville
5.0 out of 5 average rating, 202 reviewsWaterfront Getaway - View of bay from your bed
Apr 17 – 24
Apartment in Annapolis
4.89 out of 5 average rating, 19 reviewsAnnapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
Dec 7 – 14
Home in Annapolis
4.95 out of 5 average rating, 39 reviewsNaptown Suite
Jun 29 – Jul 6
Apartment in Annapolis
4.93 out of 5 average rating, 30 reviewsHillsmere Hideaway
Nov 12 – 19
Guesthouse in Annapolis
4.85 out of 5 average rating, 52 reviewsAnnapolis 1- bedroom Oasis by the Bay!
Aug 13 – 20
Guesthouse in Annapolis
4.95 out of 5 average rating, 77 reviewsPrivate Cottage on gated estate
Jun 7 – 14
Home in Annapolis
5.0 out of 5 average rating, 15 reviewsAnnapolis Cottage at Bay Ridge, Renovated 2022
Mar 16 – 23
Home in Annapolis
4.88 out of 5 average rating, 24 reviewsCute cozy rancher close to down town Annapolis
Jun 18 – 25
Cottage in Annapolis
4.96 out of 5 average rating, 50 reviewsPeaceful Escape: Bay Ridge Cottage by the Bay
Nov 2 – 9
Home in Annapolis
4.88 out of 5 average rating, 25 reviewsAnnapolis Shore House-Family retreat near the Bay
Jun 30 – Jul 7
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