Vacation rentals in Highland Beach

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 123 reviews

Waterfront 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

G$67,184 GYD per night
Guest favorite

Cottage in Annapolis

4.96 out of 5 average rating, 328 reviews

Relaxing 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

G$39,548 GYD per night
Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 308 reviews

Wright’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

G$38,996 GYD per night

Popular amenities for Highland Beach vacation rentals

Other great vacation rentals in Highland Beach

Guest favorite

Loft in Annapolis

4.91 out of 5 average rating, 911 reviews

Step Out to Main Street From a Chic Loft

Jan 13 – 20

G$30,798 GYD per night
Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 110 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Jul 15 – 22

G$32,359 GYD per night
Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

Apr 17 – 24

G$55,145 GYD per night
Superhost

Apartment in Annapolis

4.89 out of 5 average rating, 19 reviews

Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT

Dec 7 – 14

G$30,329 GYD per night
Guest favorite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

Jun 29 – Jul 6

G$26,106 GYD per night
Guest favorite

Apartment in Annapolis

4.93 out of 5 average rating, 30 reviews

Hillsmere Hideaway

Nov 12 – 19

G$26,676 GYD per night
Guest favorite

Guesthouse in Annapolis

4.85 out of 5 average rating, 52 reviews

Annapolis 1- bedroom Oasis by the Bay!

Aug 13 – 20

G$26,555 GYD per night
Guest favorite

Guesthouse in Annapolis

4.95 out of 5 average rating, 77 reviews

Private Cottage on gated estate

Jun 7 – 14

G$37,725 GYD per night
Guest favorite

Home in Annapolis

5.0 out of 5 average rating, 15 reviews

Annapolis Cottage at Bay Ridge, Renovated 2022

Mar 16 – 23

G$61,248 GYD per night
Guest favorite

Home in Annapolis

4.88 out of 5 average rating, 24 reviews

Cute cozy rancher close to down town Annapolis

Jun 18 – 25

G$28,272 GYD per night
Guest favorite

Cottage in Annapolis

4.96 out of 5 average rating, 50 reviews

Peaceful Escape: Bay Ridge Cottage by the Bay

Nov 2 – 9

G$72,529 GYD per night
Guest favorite

Home in Annapolis

4.88 out of 5 average rating, 25 reviews

Annapolis Shore House-Family retreat near the Bay

Jun 30 – Jul 7

G$102,397 GYD per night

Destinations to explore