Vacation rentals in Hillsmere Shores
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Top-rated vacation rentals in Hillsmere Shores
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Edgewater
4.99 out of 5 average rating, 122 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.
Nov 11 – 18
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!
Jun 27 – Jul 4
Guesthouse in Annapolis
4.9 out of 5 average rating, 202 reviewsCalico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.
Nov 14 – 21
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Hillsmere Shores vacation rentals
Other great vacation rentals in Hillsmere Shores
Guest suite in Arnold
4.94 out of 5 average rating, 110 reviewsCoastal Comfort Suite Near Annapolis, Hottub, EV
Sep 3 – 10
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Mar 18 – 25
Guesthouse in Galesville
4.95 out of 5 average rating, 163 reviewsGorgeous water view studio!
Jun 29 – Jul 6
Home in Annapolis
4.99 out of 5 average rating, 195 reviewsCape St Claire waterfront getaway
Sep 26 – Oct 3
Home in Annapolis
4.95 out of 5 average rating, 39 reviewsNaptown Suite
May 1 – 8
Home in Annapolis
4.88 out of 5 average rating, 24 reviewsCute cozy rancher close to down town Annapolis
Apr 29 – May 6
Apartment in Annapolis
4.93 out of 5 average rating, 30 reviewsHillsmere Hideaway
Aug 23 – 30
Guesthouse in Edgewater
5.0 out of 5 average rating, 54 reviews1 large room efficiency in detached garage.
Nov 16 – 23
Apartment in Annapolis
4.89 out of 5 average rating, 19 reviewsAnnapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
Dec 6 – 13
Guesthouse in Annapolis
4.95 out of 5 average rating, 77 reviewsPrivate Cottage on gated estate
Apr 25 – May 2
Guest suite in Riva
5.0 out of 5 average rating, 7 reviewsCozy one bedroom appt on the water
Jul 17 – 24
Guesthouse in Annapolis
4.85 out of 5 average rating, 52 reviewsAnnapolis 1- bedroom Oasis by the Bay!
Jul 30 – Aug 6
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